-
1
-
-
5244279498
-
-
For recent reviews, see: a
-
For recent reviews, see: a) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531;
-
(1993)
Chem. Rev
, vol.93
, pp. 1503-1531
-
-
Toshima, K.1
Tatsuta, K.2
-
3
-
-
0004111999
-
-
Eds, S. H. Khan, R. A. O'Neil, Harwood Academic Publishers, Amsterdam
-
c) Modern Methods in Carbohydrate Synthesis (Eds.: S. H. Khan, R. A. O'Neil), Harwood Academic Publishers, Amsterdam, 1996;
-
(1996)
Modern Methods in Carbohydrate Synthesis
-
-
-
4
-
-
0004055174
-
-
Eds, B. Ernst, G. W. Hart, P. Sinaÿ, VCH, Weinheim, Part I;
-
d) Carbohydrates in Chemistry and Biology (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), VCH, Weinheim, 2000, Part I;
-
(2000)
Carbohydrates in Chemistry and Biology
-
-
-
7
-
-
0037247972
-
-
For recent reviews, see: a
-
For recent reviews, see: a) A. V. Demchenko, Curr. Org. Chem. 2003, 7, 35-79;
-
(2003)
Curr. Org. Chem
, vol.7
, pp. 35-79
-
-
Demchenko, A.V.1
-
9
-
-
24144498474
-
-
Very recently, the (1S)-phenyl-2-(phenylsulfanyl)ethyl group was developed as an O-2 protecting group with an anchimeric assistance for the exclusive formation of α-glycosides: J.-H. Kim, H. Yang, J. Park, G.-J. Boons, J. Am. Chem. Soc. 2005, 127, 12090-12097.
-
Very recently, the (1S)-phenyl-2-(phenylsulfanyl)ethyl group was developed as an O-2 protecting group with an anchimeric assistance for the exclusive formation of α-glycosides: J.-H. Kim, H. Yang, J. Park, G.-J. Boons, J. Am. Chem. Soc. 2005, 127, 12090-12097.
-
-
-
-
10
-
-
0042671098
-
-
Kiso and co-workers reported that the 4,6-O-di-tert-butylsilylene-protected galactosyl and galactosaminyl donors exhibited good to excellent a selectivities despite the presence of C-2 functionalities capable of neighboring group participation: a A. Imamura, H. Ando, S. Korogi, G. Tanabe, O. Muraoka, H. Ishida, M. Kiso, Tetrahedron Lett. 2003, 44, 6725-6728;
-
Kiso and co-workers reported that the 4,6-O-di-tert-butylsilylene-protected galactosyl and galactosaminyl donors exhibited good to excellent a selectivities despite the presence of C-2 functionalities capable of neighboring group participation: a) A. Imamura, H. Ando, S. Korogi, G. Tanabe, O. Muraoka, H. Ishida, M. Kiso, Tetrahedron Lett. 2003, 44, 6725-6728;
-
-
-
-
11
-
-
33845212293
-
-
b) A. Imamura, A. Kimura, H. Ando, H. Ishida, M. Kiso, Chem. Eur. J. 2006, 12, 8862-8870.
-
(2006)
Chem. Eur. J
, vol.12
, pp. 8862-8870
-
-
Imamura, A.1
Kimura, A.2
Ando, H.3
Ishida, H.4
Kiso, M.5
-
12
-
-
33847801270
-
-
R. U. Lemieux, K. B. Hendriks, R. V. Stick, K. James, J. Am. Chem. Soc. 1975, 97, 4056-4062.
-
(1975)
J. Am. Chem. Soc
, vol.97
, pp. 4056-4062
-
-
Lemieux, R.U.1
Hendriks, K.B.2
Stick, R.V.3
James, K.4
-
13
-
-
0015970036
-
-
For reviews that include discussions regarding the effect of ethereal solvents, see: a
-
For reviews that include discussions regarding the effect of ethereal solvents, see: a) G. Wulff, G. Röhle, Angew. Chem. 1974, 86, 173-187;
-
(1974)
Angew. Chem
, vol.86
, pp. 173-187
-
-
Wulff, G.1
Röhle, G.2
-
16
-
-
48749140248
-
-
For representative examples of the use of ether, which leads to the formation of an α-glycosidic linkage, see: a
-
For representative examples of the use of ether, which leads to the formation of an α-glycosidic linkage, see: a) S. Hashimoto, M. Hayashi, R. Noyori, Tetrahedron Lett. 1984, 25, 1379-1382;
-
(1984)
Tetrahedron Lett
, vol.25
, pp. 1379-1382
-
-
Hashimoto, S.1
Hayashi, M.2
Noyori, R.3
-
20
-
-
0242631685
-
-
2O: a K. Igarashi, T. Honma, J. Irisawa, Carbohydr. Res. 1970, 15, 329-337;
-
2O: a) K. Igarashi, T. Honma, J. Irisawa, Carbohydr. Res. 1970, 15, 329-337;
-
-
-
-
21
-
-
1542638740
-
-
b) K. Igarashi, J. Irisawa, T. Honma, Carbohydr. Res. 1975, 39, 213-225.
-
(1975)
Carbohydr. Res
, vol.39
, pp. 213-225
-
-
Igarashi, K.1
Irisawa, J.2
Honma, T.3
-
24
-
-
45549115621
-
-
c) T. Matsumoto, H. Maeta, K. Suzuki, G. Tsuchihashi, Tetrahedron Lett. 1988, 29, 3567-3570;
-
(1988)
Tetrahedron Lett
, vol.29
, pp. 3567-3570
-
-
Matsumoto, T.1
Maeta, H.2
Suzuki, K.3
Tsuchihashi, G.4
-
26
-
-
0029058108
-
-
e) W.-S. Kim, S. Hosono, H. Sasai, M. Shibasaki, Tetrahedron Lett. 1995, 36, 4443-4446;
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 4443-4446
-
-
Kim, W.-S.1
Hosono, S.2
Sasai, H.3
Shibasaki, M.4
-
28
-
-
0012862794
-
-
g) K. Fukase, Y. Nakai, T. Kanoh, S. Kusumoto, Synlett 1998, 84-86;
-
(1998)
Synlett
, pp. 84-86
-
-
Fukase, K.1
Nakai, Y.2
Kanoh, T.3
Kusumoto, S.4
-
29
-
-
0033450741
-
-
h) M. Wakao, Y. Nakai, K. Fukase, S. Kusumoto, Chem. Lett. 1999, 27-28;
-
(1999)
Chem. Lett
, pp. 27-28
-
-
Wakao, M.1
Nakai, Y.2
Fukase, K.3
Kusumoto, S.4
-
30
-
-
0033520244
-
-
i) A. V. Demchenko, E. Rousson, G.-J. Boons, Tetrahedron Lett. 1999, 40, 6523-6526;
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 6523-6526
-
-
Demchenko, A.V.1
Rousson, E.2
Boons, G.-J.3
-
32
-
-
0035982963
-
-
k) T. Mukaiyama, M. Suenaga, H. Chiba, H. Jona, Chem. Lett. 2002, 56-57;
-
(2002)
Chem. Lett
, pp. 56-57
-
-
Mukaiyama, T.1
Suenaga, M.2
Chiba, H.3
Jona, H.4
-
33
-
-
0036184540
-
-
l) H. Jona, H. Mandai, W. Chavasiri, K. Takeuchi, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2002, 75, 291-309;
-
(2002)
Bull. Chem. Soc. Jpn
, vol.75
, pp. 291-309
-
-
Jona, H.1
Mandai, H.2
Chavasiri, W.3
Takeuchi, K.4
Mukaiyama, T.5
-
34
-
-
28844505985
-
-
m) J. Matsuo, T. Shirahata, S. Ōmura, Tetrahedron Lett. 2006, 47, 267-271.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 267-271
-
-
Matsuo, J.1
Shirahata, T.2
Ōmura, S.3
-
36
-
-
0032844913
-
-
b) S. C. Ennis, A. J. Fairbanks, R. J. Tennant-Eyles, H. S. Yeates, Synlett 1999, 1387-1390;
-
(1999)
Synlett
, pp. 1387-1390
-
-
Ennis, S.C.1
Fairbanks, A.J.2
Tennant-Eyles, R.J.3
Yeates, H.S.4
-
37
-
-
0034617802
-
-
c) C. M. P. Seward, I. Cumpstey, M. Aloui, S. C. Ennis, A. J. Redgrave, A. J. Fairbanks, Chem. Commun. 2000, 1409-1410;
-
(2000)
Chem. Commun
, pp. 1409-1410
-
-
Seward, C.M.P.1
Cumpstey, I.2
Aloui, M.3
Ennis, S.C.4
Redgrave, A.J.5
Fairbanks, A.J.6
-
38
-
-
0035931404
-
-
d) T. Ziegler, G. Lemanski, J. Hürttlen, Tetrahedron Lett. 2001, 42, 569-572;
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 569-572
-
-
Ziegler, T.1
Lemanski, G.2
Hürttlen, J.3
-
40
-
-
0035821369
-
-
f) S. C. Ennis, A. J. Fairbanks, C. A. Slinn, R. J. Tennant-Eyles, H. S. Yeates, Tetrahedron 2001, 57, 4221-4230.
-
(2001)
Tetrahedron
, vol.57
, pp. 4221-4230
-
-
Ennis, S.C.1
Fairbanks, A.J.2
Slinn, C.A.3
Tennant-Eyles, R.J.4
Yeates, H.S.5
-
41
-
-
0342936076
-
-
For reviews, see: a
-
For reviews, see: a) K.-H. Jung, M. Müller, R. R. Schmidt, Chem. Rev. 2000, 100, 4423-4442;
-
(2000)
Chem. Rev
, vol.100
, pp. 4423-4442
-
-
Jung, K.-H.1
Müller, M.2
Schmidt, R.R.3
-
44
-
-
0030915322
-
-
b) G.-J. Boons, S. Bowers, D. M. Coe, Tetrahedron Lett. 1997, 38, 3773-3776;
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 3773-3776
-
-
Boons, G.-J.1
Bowers, S.2
Coe, D.M.3
-
45
-
-
12944303102
-
-
c) H. Tokimoto, Y. Fujimoto, K. Fukase, S. Kusumoto, Tetrahedron: Asymmetry 2005, 16, 441-447.
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 441-447
-
-
Tokimoto, H.1
Fujimoto, Y.2
Fukase, K.3
Kusumoto, S.4
-
46
-
-
0347482882
-
-
H. A. Orgueira, A. Bartolozzi, P. Schell, P. H. Seeberger, Angew. Chem. 2002, 114, 2232-2235;
-
(2002)
Angew. Chem
, vol.114
, pp. 2232-2235
-
-
Orgueira, H.A.1
Bartolozzi, A.2
Schell, P.3
Seeberger, P.H.4
-
47
-
-
0037124658
-
-
Angew. Chem. Int. Ed. 2002, 41, 2128-2131.
-
(2002)
Angew. Chem. Int. Ed
, vol.41
, pp. 2128-2131
-
-
-
49
-
-
0037152265
-
-
b) Y.-P. Cheng, H.-T. Chen, C.-C. Lin, Tetrahedron Lett. 2002, 43, 7721-7723;
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 7721-7723
-
-
Cheng, Y.-P.1
Chen, H.-T.2
Lin, C.-C.3
-
50
-
-
33645793829
-
-
c) N. Ustyuzhanina, B. Komarova, N. Zlotina, V. Krylov, A. Gerbst, Y. Tsvetkov, N. Nifantiev, Synlett 2006, 921-923;
-
(2006)
Synlett
, pp. 921-923
-
-
Ustyuzhanina, N.1
Komarova, B.2
Zlotina, N.3
Krylov, V.4
Gerbst, A.5
Tsvetkov, Y.6
Nifantiev, N.7
-
51
-
-
33646897137
-
-
d) A. Ishiwata, S. Ohta, Y. Ito, Carbohydr. Res. 2006, 341, 1557-1573.
-
(2006)
Carbohydr. Res
, vol.341
, pp. 1557-1573
-
-
Ishiwata, A.1
Ohta, S.2
Ito, Y.3
-
52
-
-
37049086359
-
-
For the use of diphenyl phosphate as a leaving group, see: a
-
For the use of diphenyl phosphate as a leaving group, see: a) S. Hashimoto, T. Honda, S. Ikegami, J. Chem. Soc. Chem. Commun. 1989, 685-687;
-
(1989)
J. Chem. Soc. Chem. Commun
, pp. 685-687
-
-
Hashimoto, S.1
Honda, T.2
Ikegami, S.3
-
53
-
-
0042197225
-
-
b) T. Tsuda, S. Nakamura, S. Hashimoto, Tetrahedron Lett. 2003, 44, 6453-6457;
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 6453-6457
-
-
Tsuda, T.1
Nakamura, S.2
Hashimoto, S.3
-
54
-
-
5644241800
-
-
c) T. Tsuda, S. Nakamura, S. Hashimoto, Tetrahedron 2004, 60, 10711-10737.
-
(2004)
Tetrahedron
, vol.60
, pp. 10711-10737
-
-
Tsuda, T.1
Nakamura, S.2
Hashimoto, S.3
-
55
-
-
0001409217
-
-
For the use of P,P-diphenyl-N-(p-toluenesulfonyl) phosphinimidate as a leaving group, see: a) S. Hashimoto, T. Honda, S. Ikegami, Heterocycles 1990, 30, 775-778;
-
For the use of P,P-diphenyl-N-(p-toluenesulfonyl) phosphinimidate as a leaving group, see: a) S. Hashimoto, T. Honda, S. Ikegami, Heterocycles 1990, 30, 775-778;
-
-
-
-
56
-
-
0025010913
-
-
b) S. Hashimoto, T. Honda, S. Ikegami, Chem. Pharm. Bull. 1990, 38, 2323-2325;
-
(1990)
Chem. Pharm. Bull
, vol.38
, pp. 2323-2325
-
-
Hashimoto, S.1
Honda, T.2
Ikegami, S.3
-
57
-
-
0026061989
-
-
c) S. Hashimoto, T. Honda, S. Ikegami, Tetrahedron Lett. 1991, 32, 1653-1654.
-
(1991)
Tetrahedron Lett
, vol.32
, pp. 1653-1654
-
-
Hashimoto, S.1
Honda, T.2
Ikegami, S.3
-
58
-
-
0025327537
-
-
For the use of N,N,N′,N′-tetramethyl-N″-phenylphosphorodiamidimidothioate as a leaving group, see: S. Hashimoto, T. Honda, S. Ikegami, Tetrahedron Lett. 1990, 31, 4769-4772.
-
For the use of N,N,N′,N′-tetramethyl-N″-phenylphosphorodiamidimidothioate as a leaving group, see: S. Hashimoto, T. Honda, S. Ikegami, Tetrahedron Lett. 1990, 31, 4769-4772.
-
-
-
-
59
-
-
0026780175
-
-
For the use of N,N,N′,N′- tetramethylphosphorodiamidate as a leaving group, see: a S. Hashimoto, Y. Yanagiya, T. Honda, H. Harada, S. Ikegami, Tetrahedron Lett. 1992, 33, 3523-3526;
-
For the use of N,N,N′,N′- tetramethylphosphorodiamidate as a leaving group, see: a) S. Hashimoto, Y. Yanagiya, T. Honda, H. Harada, S. Ikegami, Tetrahedron Lett. 1992, 33, 3523-3526;
-
-
-
-
60
-
-
0002623044
-
-
b) S. Hashimoto, Y. Yanagiya, T. Honda, S. Ikegami, Chem. Lett. 1992, 1511-1514;
-
(1992)
Chem. Lett
, pp. 1511-1514
-
-
Hashimoto, S.1
Yanagiya, Y.2
Honda, T.3
Ikegami, S.4
-
61
-
-
0142142314
-
-
c) T. Iimori, H. Kobayashi, S. Hashimoto, S. Ikegami, Heterocycles 1996, 42, 485-488.
-
(1996)
Heterocycles
, vol.42
, pp. 485-488
-
-
Iimori, T.1
Kobayashi, H.2
Hashimoto, S.3
Ikegami, S.4
-
62
-
-
0028944426
-
-
For the use of diethyl phosphite as a leaving group, see: a
-
For the use of diethyl phosphite as a leaving group, see: a) S. Hashimoto, K. Umeo, A. Sano, N. Watanabe, M. Nakajima, S. Ikegami, Tetrahedron Lett. 1995, 36, 2251-2254;
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 2251-2254
-
-
Hashimoto, S.1
Umeo, K.2
Sano, A.3
Watanabe, N.4
Nakajima, M.5
Ikegami, S.6
-
63
-
-
85066087038
-
-
b) S. Hashimoto, A. Sano, H. Sakamoto, M. Nakajima, Y. Yanagiya, S. Ikegami, Synlett 1995, 1271-1273;
-
(1995)
Synlett
, pp. 1271-1273
-
-
Hashimoto, S.1
Sano, A.2
Sakamoto, H.3
Nakajima, M.4
Yanagiya, Y.5
Ikegami, S.6
-
64
-
-
0029591764
-
-
c) S. Hashimoto, A. Sano, K. Umeo, M. Nakajima, S. Ikegami, Chem. Pharm. Bull. 1995, 43, 2267-2269;
-
(1995)
Chem. Pharm. Bull
, vol.43
, pp. 2267-2269
-
-
Hashimoto, S.1
Sano, A.2
Umeo, K.3
Nakajima, M.4
Ikegami, S.5
-
65
-
-
0012572116
-
-
d) S. Hashimoto, J. Inagaki, H. Sakamoto, A. Sano, M. Nakajima, Heterocycles 1997, 46, 215-220;
-
(1997)
Heterocycles
, vol.46
, pp. 215-220
-
-
Hashimoto, S.1
Inagaki, J.2
Sakamoto, H.3
Sano, A.4
Nakajima, M.5
-
66
-
-
0033532915
-
-
e) H. Tanaka, H. Sakamoto, A. Sano, S. Nakamura, M. Nakajima, S. Hashimoto, Chem. Commun. 1999, 1259-1260;
-
(1999)
Chem. Commun
, pp. 1259-1260
-
-
Tanaka, H.1
Sakamoto, H.2
Sano, A.3
Nakamura, S.4
Nakajima, M.5
Hashimoto, S.6
-
67
-
-
0032793233
-
-
f) J. Inagaki, H. Sakamoto, M. Nakajima, S. Nakamura, S. Hashimoto, Synlett 1999, 1274-1276;
-
(1999)
Synlett
, pp. 1274-1276
-
-
Inagaki, J.1
Sakamoto, H.2
Nakajima, M.3
Nakamura, S.4
Hashimoto, S.5
-
68
-
-
0037344398
-
-
g) T. Tsuda, S. Sato, S. Nakamura, S. Hashimoto, Heterocycles 2003, 59, 509-515;
-
(2003)
Heterocycles
, vol.59
, pp. 509-515
-
-
Tsuda, T.1
Sato, S.2
Nakamura, S.3
Hashimoto, S.4
-
69
-
-
54849407754
-
-
h) R. Arihara, S. Nakamura, S. Hashimoto, Angew. Chem. 2005, 117, 2285-2289;
-
(2005)
Angew. Chem
, vol.117
, pp. 2285-2289
-
-
Arihara, R.1
Nakamura, S.2
Hashimoto, S.3
-
70
-
-
17644412385
-
-
Angew. Chem. Int. Ed. 2005, 44, 2245-2249;
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 2245-2249
-
-
-
71
-
-
26244435768
-
-
i) T. Tsuda, R. Arihara, S. Sato, M. Koshiba, S. Nakamura, S. Hashimoto, Tetrahedron 2005, 61, 10719-10733.
-
(2005)
Tetrahedron
, vol.61
, pp. 10719-10733
-
-
Tsuda, T.1
Arihara, R.2
Sato, S.3
Koshiba, M.4
Nakamura, S.5
Hashimoto, S.6
-
72
-
-
0030848902
-
-
For chemoselective glycosidation strategies capitalizing on phosphorus-containing leaving groups, see: a
-
For chemoselective glycosidation strategies capitalizing on phosphorus-containing leaving groups, see: a) S. Hashimoto, H. Sakamoto, T. Honda, S. Ikegami, Tetrahedron Lett. 1997, 38, 5181-5184;
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 5181-5184
-
-
Hashimoto, S.1
Sakamoto, H.2
Honda, T.3
Ikegami, S.4
-
73
-
-
0030830477
-
-
b) S. Hashimoto, H. Sakamoto, T. Honda, H. Abe, S. Nakamura, S. Ikegami, Tetrahedron Lett. 1997, 38, 8969-8972;
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 8969-8972
-
-
Hashimoto, S.1
Sakamoto, H.2
Honda, T.3
Abe, H.4
Nakamura, S.5
Ikegami, S.6
-
74
-
-
0034734698
-
-
c) H. Sakamoto, S. Nakamura, T. Tsuda, S. Hashimoto, Tetrahedron Lett. 2000, 41, 7691-7695.
-
(2000)
Tetrahedron Lett
, vol.41
, pp. 7691-7695
-
-
Sakamoto, H.1
Nakamura, S.2
Tsuda, T.3
Hashimoto, S.4
-
75
-
-
0004055174
-
-
For reviews on glycosidations of glycosyl phosphates, phosphites and other O-P derivatives, see: a, Eds, B. Ernst, G. W. Hart, P. Sinaÿ, VCH, Weinheim, Part I, pp
-
For reviews on glycosidations of glycosyl phosphates, phosphites and other O-P derivatives, see: a) Z. Zhang, C.-H. Wong in Carbohydrates in Chemistry and Biology (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), VCH, Weinheim, 2000, Part I, pp. 117-134;
-
(2000)
Carbohydrates in Chemistry and Biology
, pp. 117-134
-
-
Zhang, Z.1
Wong, C.-H.2
-
78
-
-
54849434188
-
-
Ed, A. V. Demchenko, VCH, Weinheim
-
d) S. Nakamura, H. Nambu, S. Hashimoto in Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance (Ed.: A. V. Demchenko), VCH, Weinheim, 2008, pp. 223-259.
-
(2008)
Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance
, pp. 223-259
-
-
Nakamura, S.1
Nambu, H.2
Hashimoto, S.3
-
81
-
-
0002869847
-
-
Glycosyl iodides were prepared and used as donors for the preparation of α-glycosides: a F. J. Kronzer, C. Schuerch, Carbohydr. Res. 1974, 34, 71- 78;
-
Glycosyl iodides were prepared and used as donors for the preparation of α-glycosides: a) F. J. Kronzer, C. Schuerch, Carbohydr. Res. 1974, 34, 71- 78;
-
-
-
-
84
-
-
0037144691
-
-
2O (1:4) at low temperature (-78→-20°C), but the scope of the reaction has not been explored: F. Bosse, L. A. Marcaurelle, P. H. Seeberger, J. Org. Chem. 2002, 67, 6659-6670.
-
2O (1:4) at low temperature (-78→-20°C), but the scope of the reaction has not been explored: F. Bosse, L. A. Marcaurelle, P. H. Seeberger, J. Org. Chem. 2002, 67, 6659-6670.
-
-
-
-
86
-
-
33747397597
-
-
T. Saitoh, S. Yoshida, J. Ichikawa, J. Org. Chem. 2006, 71, 6414-6419.
-
(2006)
J. Org. Chem
, vol.71
, pp. 6414-6419
-
-
Saitoh, T.1
Yoshida, S.2
Ichikawa, J.3
-
87
-
-
33751157840
-
-
For the use of Brønsted acids as promoters in glycosidations with glycosyl phosphites, see: a
-
For the use of Brønsted acids as promoters in glycosidations with glycosyl phosphites, see: a) H. Kondo, S. Aoki, Y. Ichikawa, R. L. Halcomb, H. Ritzen, C.-H. Wong, J. Org. Chem. 1994, 59, 864-877;
-
(1994)
J. Org. Chem
, vol.59
, pp. 864-877
-
-
Kondo, H.1
Aoki, S.2
Ichikawa, Y.3
Halcomb, R.L.4
Ritzen, H.5
Wong, C.-H.6
-
88
-
-
54849425128
-
-
reference [19e];
-
b) reference [19e];
-
-
-
-
89
-
-
54849409464
-
-
4 to activate a glycosyl diethyl phosphite, see reference [19 h].
-
4 to activate a glycosyl diethyl phosphite, see reference [19 h].
-
-
-
-
90
-
-
54849425753
-
-
The remarkable α-directing effect of dioxane has already been documented by Boons and co-workers: a reference [9f];
-
The remarkable α-directing effect of dioxane has already been documented by Boons and co-workers: a) reference [9f];
-
-
-
-
91
-
-
54849406979
-
-
reference [9i
-
b) reference [9i].
-
-
-
-
92
-
-
0035802334
-
-
Seeberger and co-workers demonstrated that the glycosidation reaction of a glycosyl dibutyl phosphate with a TMS ether proceeded to completion by the use of 1 mol% of TfOH as a promoter, since TMSOTf, generated in situ along with the desilylated alcohol, functioned as an actual promoter for the formation of the 1,2-trans-β-glycoside from glycosyl dibutyl phosphate: O. J. Plante, E. R. Palmacci, R. B. Andrade, P. H. Seeberger, J. Am. Chem. Soc. 2001, 123, 9545-9554
-
Seeberger and co-workers demonstrated that the glycosidation reaction of a glycosyl dibutyl phosphate with a TMS ether proceeded to completion by the use of 1 mol% of TfOH as a promoter, since TMSOTf, generated in situ along with the desilylated alcohol, functioned as an actual promoter for the formation of the 1,2-trans-β-glycoside from glycosyl dibutyl phosphate: O. J. Plante, E. R. Palmacci, R. B. Andrade, P. H. Seeberger, J. Am. Chem. Soc. 2001, 123, 9545-9554.
-
-
-
-
93
-
-
54849411232
-
-
4 solution in the reaction of diethyl phosphite 2 with alcohol 3 exhibited diminished α selectivity (α/β= 85:15), again demonstrating the superiority of phosphate 1 over phosphite 2.
-
4 solution in the reaction of diethyl phosphite 2 with alcohol 3 exhibited diminished α selectivity (α/β= 85:15), again demonstrating the superiority of phosphate 1 over phosphite 2.
-
-
-
-
95
-
-
0025020337
-
-
b) R. R. Schmidt, H. Gaden, H. Jatzke, Tetrahedron Lett. 1990, 31, 327-330;
-
(1990)
Tetrahedron Lett
, vol.31
, pp. 327-330
-
-
Schmidt, R.R.1
Gaden, H.2
Jatzke, H.3
-
96
-
-
0001943060
-
-
Eds, H. Ogura, A. Hasegawa, T. Suami, VCH, Weinheim
-
c) R. R. Schmidt in Carbohydrates - Synthetic Methods and Applications in Medicinal Chemistry (Eds.: H. Ogura, A. Hasegawa, T. Suami), VCH, Weinheim, 1992, pp. 66-88;
-
(1992)
Carbohydrates - Synthetic Methods and Applications in Medicinal Chemistry
, pp. 66-88
-
-
Schmidt, R.R.1
-
98
-
-
54849437489
-
-
A control experiment revealed that anomer equilibration of diphenyl phosphate 1 (α/β=1:99) was effected within 30 seconds under the optimized conditions to give a 98:2 equilibrium mixture in favor of the thermodynamically more stable α anomer 1α.
-
A control experiment revealed that anomer equilibration of diphenyl phosphate 1 (α/β=1:99) was effected within 30 seconds under the optimized conditions to give a 98:2 equilibrium mixture in favor of the thermodynamically more stable α anomer 1α.
-
-
-
-
99
-
-
54849409874
-
-
[31a]
-
[31a]
-
-
-
-
100
-
-
54849433789
-
-
Glycosidation of phosphate 1 with reactive alcohol 3 proceeded to 90% conversion during the 30 s period.
-
Glycosidation of phosphate 1 with reactive alcohol 3 proceeded to 90% conversion during the 30 s period.
-
-
-
-
101
-
-
0001397662
-
-
T. Matsumoto, M. Katsuki, K. Suzuki, Tetrahedron Lett. 1988, 29, 6935-6938.
-
(1988)
Tetrahedron Lett
, vol.29
, pp. 6935-6938
-
-
Matsumoto, T.1
Katsuki, M.2
Suzuki, K.3
-
102
-
-
0033518559
-
-
Wong and co-workers reported that the per-O-benzyl-protected thiogalactoside is 6.4-fold more active than the corresponding thioglucoside probably owing to the stereo- and inductive effects and possible involvement of the axial 4-O lone pair electrons in the stabilization of the oxocarbenium ion intermediate: Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734-753.
-
Wong and co-workers reported that the per-O-benzyl-protected thiogalactoside is 6.4-fold more active than the corresponding thioglucoside probably owing to the stereo- and inductive effects and possible involvement of the axial 4-O lone pair electrons in the stabilization of the oxocarbenium ion intermediate: Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734-753.
-
-
-
-
103
-
-
54849432585
-
-
2Cl>-NPhth>-OBz>-OBn.
-
2Cl>-NPhth>-OBz>-OBn.
-
-
-
-
104
-
-
0027177356
-
-
a) T. Natori, Y. Koezuka, T. Higa, Tetrahedron Lett. 1993, 34, 5591-5592;
-
(1993)
Tetrahedron Lett
, vol.34
, pp. 5591-5592
-
-
Natori, T.1
Koezuka, Y.2
Higa, T.3
-
105
-
-
0027160611
-
-
b) K. Akimoto, T. Natori, M. Morita, Tetrahedron Lett. 1993, 34, 5593-5596;
-
(1993)
Tetrahedron Lett
, vol.34
, pp. 5593-5596
-
-
Akimoto, K.1
Natori, T.2
Morita, M.3
-
106
-
-
0028204397
-
-
c) T. Natori, M. Morita, K. Akimoto, Y. Koezuka, Tetrahedron 1994, 50, 2771-2784.
-
(1994)
Tetrahedron
, vol.50
, pp. 2771-2784
-
-
Natori, T.1
Morita, M.2
Akimoto, K.3
Koezuka, Y.4
-
107
-
-
0029062153
-
-
a) M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, H. Fukushima, J. Med. Chem. 1995, 38, 2176-2187;
-
(1995)
J. Med. Chem
, vol.38
, pp. 2176-2187
-
-
Morita, M.1
Motoki, K.2
Akimoto, K.3
Natori, T.4
Sakai, T.5
Sawa, E.6
Yamaji, K.7
Koezuka, Y.8
Kobayashi, E.9
Fukushima, H.10
-
108
-
-
0028957618
-
-
b) M. Morita, T. Natori, K. Akimoto, T. Osawa, H. Fukushima, Y. Koezuka, Bioorg. Med. Chem. Lett. 1995, 5, 699-704;
-
(1995)
Bioorg. Med. Chem. Lett
, vol.5
, pp. 699-704
-
-
Morita, M.1
Natori, T.2
Akimoto, K.3
Osawa, T.4
Fukushima, H.5
Koezuka, Y.6
-
109
-
-
0028986518
-
-
c) K. Motoki, E. Kobayashi, T. Uchida, H. Fukushima, Y. Koezuka, Bioorg. Med. Chem. Lett. 1995, 5, 705-710;
-
(1995)
Bioorg. Med. Chem. Lett
, vol.5
, pp. 705-710
-
-
Motoki, K.1
Kobayashi, E.2
Uchida, T.3
Fukushima, H.4
Koezuka, Y.5
-
110
-
-
0029882597
-
-
d) E. Kobayashi, K. Motoki, Y. Yamaguchi, T. Uchida, H. Fukushima, Y. Koezuka, Bioorg. Med. Chem. 1996, 4, 615-619.
-
(1996)
Bioorg. Med. Chem
, vol.4
, pp. 615-619
-
-
Kobayashi, E.1
Motoki, K.2
Yamaguchi, Y.3
Uchida, T.4
Fukushima, H.5
Koezuka, Y.6
-
111
-
-
0030696696
-
-
T. Kawano, J. Cui, Y. Koezuka, I. Toura, Y. Kaneko, K. Motoki, H. Ueno, R. Nakagawa, H. Sato, E. Kondo, H. Koseki, M. Taniguchi, Science 1997, 278, 1626-1629.
-
(1997)
Science
, vol.278
, pp. 1626-1629
-
-
Kawano, T.1
Cui, J.2
Koezuka, Y.3
Toura, I.4
Kaneko, Y.5
Motoki, K.6
Ueno, H.7
Nakagawa, R.8
Sato, H.9
Kondo, E.10
Koseki, H.11
Taniguchi, M.12
-
112
-
-
18044392378
-
-
For recent reviews, see: a
-
For recent reviews, see: a) C. R. Berkers, H. Ovaa, Trends Pharmacol. Sci. 2005, 26, 252-257;
-
(2005)
Trends Pharmacol. Sci
, vol.26
, pp. 252-257
-
-
Berkers, C.R.1
Ovaa, H.2
-
113
-
-
33747835875
-
-
b) P. B. Savage, L. Teyton, A. Bendelac, Chem. Soc. Rev. 2006, 35, 771-779.
-
(2006)
Chem. Soc. Rev
, vol.35
, pp. 771-779
-
-
Savage, P.B.1
Teyton, L.2
Bendelac, A.3
-
114
-
-
54849430151
-
-
Kirin group: a reference [39a];
-
Kirin group: a) reference [39a];
-
-
-
-
115
-
-
0001413882
-
-
b) M. Morita, E. Sawa, K. Yamaji, T. Sakai, T. Natori, Y. Koezuka, H. Fukushima, K. Akimoto, Biosci. Biotechnol. Biochem. 1996, 60, 288-292;
-
(1996)
Biosci. Biotechnol. Biochem
, vol.60
, pp. 288-292
-
-
Morita, M.1
Sawa, E.2
Yamaji, K.3
Sakai, T.4
Natori, T.5
Koezuka, Y.6
Fukushima, H.7
Akimoto, K.8
-
116
-
-
0032568385
-
-
Mori group: c H. Takikawa, S. Muto, K. Mori, Tetrahedron 1998, 54, 3141-3150;
-
Mori group: c) H. Takikawa, S. Muto, K. Mori, Tetrahedron 1998, 54, 3141-3150;
-
-
-
-
117
-
-
0038399264
-
-
Schmidt group: d S. Figueroa-Pérez, R. R. Schmidt, Carbohydr. Res. 2000, 328, 95- 102;
-
Schmidt group: d) S. Figueroa-Pérez, R. R. Schmidt, Carbohydr. Res. 2000, 328, 95- 102;
-
-
-
-
118
-
-
0037189212
-
-
Wong group: e O. Plettenburg, V. Bodmer-Narkevitch, C.-H. Wong, J. Org. Chem. 2002, 67, 4559-4564;
-
Wong group: e) O. Plettenburg, V. Bodmer-Narkevitch, C.-H. Wong, J. Org. Chem. 2002, 67, 4559-4564;
-
-
-
-
119
-
-
54849423000
-
-
Kim group: f S. Kim, S. Song, T. Lee, S. Jung, D. Kim, Synthesis 2004, 847-850;
-
Kim group: f) S. Kim, S. Song, T. Lee, S. Jung, D. Kim, Synthesis 2004, 847-850;
-
-
-
-
120
-
-
54849412071
-
-
Lin group: g G.-T. Fan, Y. Pan, K.-C. Lu, Y.-P. Cheng, W.-C. Lin, S. Lin, C.-H. Lin, C.-H. Wong, J.-M. Fang, C.-C. Lin, Tetrahedron 2005, 61, 1855-1862;
-
Lin group: g) G.-T. Fan, Y. Pan, K.-C. Lu, Y.-P. Cheng, W.-C. Lin, S. Lin, C.-H. Lin, C.-H. Wong, J.-M. Fang, C.-C. Lin, Tetrahedron 2005, 61, 1855-1862;
-
-
-
-
121
-
-
19544385277
-
-
Gervay-Hague group: h W. Du, J. Gervay-Hague, Org. Lett. 2005, 7, 2063-2065;
-
Gervay-Hague group: h) W. Du, J. Gervay-Hague, Org. Lett. 2005, 7, 2063-2065;
-
-
-
-
122
-
-
32144457341
-
-
Hung group: i S.-Y. Luo, S. S. Kulkarni, C.-H. Chou, W.-M. Liao, S.-C. Hung, J. Org. Chem. 2006, 71, 1226-1229;
-
Hung group: i) S.-Y. Luo, S. S. Kulkarni, C.-H. Chou, W.-M. Liao, S.-C. Hung, J. Org. Chem. 2006, 71, 1226-1229;
-
-
-
-
123
-
-
33644788298
-
-
Wang group: j C. Xia, Q. Yao, J. Schümann, E. Rossy, W. Chen, L. Zhu, W. Zhang, G. De Libero, P. G. Wang, Bioorg. Med. Chem. Lett. 2006, 16, 2195-2199;
-
Wang group: j) C. Xia, Q. Yao, J. Schümann, E. Rossy, W. Chen, L. Zhu, W. Zhang, G. De Libero, P. G. Wang, Bioorg. Med. Chem. Lett. 2006, 16, 2195-2199;
-
-
-
-
124
-
-
33749344100
-
-
Kiso group: k A. Kimura, A. Imamura, H. Ando, H. Ishida, M. Kiso, Synlett 2006, 2379-2382;
-
Kiso group: k) A. Kimura, A. Imamura, H. Ando, H. Ishida, M. Kiso, Synlett 2006, 2379-2382;
-
-
-
-
125
-
-
33750628134
-
-
Painter group: l A. Lee, K. J. Farrand, N. Dickgreber, C. M. Hayman, S. Jürs, I. F. Hermans, G. F. Painter, Carbohydr. Res. 2006, 341, 2785-2798;
-
Painter group: l) A. Lee, K. J. Farrand, N. Dickgreber, C. M. Hayman, S. Jürs, I. F. Hermans, G. F. Painter, Carbohydr. Res. 2006, 341, 2785-2798;
-
-
-
-
126
-
-
34347401668
-
-
Ito group: m T. Tsujimoto, Y. Ito, Tetrahedron Lett. 2007, 48, 5513-5516.
-
Ito group: m) T. Tsujimoto, Y. Ito, Tetrahedron Lett. 2007, 48, 5513-5516.
-
-
-
-
132
-
-
0006644455
-
-
For evidence supporting formation of oxonium ion intermediates by participation of THF, see: a
-
For evidence supporting formation of oxonium ion intermediates by participation of THF, see: a) B. Helferich, J. Zirner, Chem. Ber. 1963, 96, 374;
-
(1963)
Chem. Ber
, vol.96
, pp. 374
-
-
Helferich, B.1
Zirner, J.2
-
134
-
-
0001663502
-
-
c) J. Tamura, S. Horito, J. Yoshimura, H. Hashimoto, Carbohydr. Res. 1990, 207, 153-165;
-
(1990)
Carbohydr. Res
, vol.207
, pp. 153-165
-
-
Tamura, J.1
Horito, S.2
Yoshimura, J.3
Hashimoto, H.4
-
137
-
-
0001943060
-
-
Eds, H. Ogura, A. Hasegawa, T. Suami, VCH, Weinheim
-
R. R. Schmidt in Carbohydrates - Synthetic Methods and Applications in Medicinal Chemistry (Eds.: H. Ogura, A. Hasegawa, T. Suami), VCH, Weinheim, 1992, pp. 66-88.
-
(1992)
Carbohydrates - Synthetic Methods and Applications in Medicinal Chemistry
, pp. 66-88
-
-
Schmidt, R.R.1
-
143
-
-
0026424324
-
-
K. Takeo, Y. Teramoto, Y. Shimono, Carbohydr. Res. 1991, 209, 167-179.
-
(1991)
Carbohydr. Res
, vol.209
, pp. 167-179
-
-
Takeo, K.1
Teramoto, Y.2
Shimono, Y.3
-
144
-
-
0039041503
-
-
a) G. Wulff, U. Schröder, J. Wichelhaus, Carbohydr. Res. 1979, 72, 280-284;
-
(1979)
Carbohydr. Res
, vol.72
, pp. 280-284
-
-
Wulff, G.1
Schröder, U.2
Wichelhaus, J.3
-
147
-
-
33744518367
-
-
b) H. Imagawa, A. Kinoshita, T. Fukuyama, H. Yamamoto, M. Nishizawa, Tetrahedron Lett. 2006, 47, 4729-4731.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 4729-4731
-
-
Imagawa, H.1
Kinoshita, A.2
Fukuyama, T.3
Yamamoto, H.4
Nishizawa, M.5
-
149
-
-
0000455256
-
-
b) S. Koto, N. Morishima, M. Araki, T. Tsuchiya, S. Zen, Bull. Chem. Soc. Jpn. 1981, 54, 1895-1896.
-
(1981)
Bull. Chem. Soc. Jpn
, vol.54
, pp. 1895-1896
-
-
Koto, S.1
Morishima, N.2
Araki, M.3
Tsuchiya, T.4
Zen, S.5
-
150
-
-
0000300180
-
-
A. Marra, J. Esnault, A. Veyrières, P. Sinaÿ, J. Am. Chem. Soc. 1992, 114, 6354-6360.
-
(1992)
J. Am. Chem. Soc
, vol.114
, pp. 6354-6360
-
-
Marra, A.1
Esnault, J.2
Veyrières, A.3
Sinaÿ, P.4
-
151
-
-
27144451469
-
-
B. Mukhopadhyay, P. Cura, K. P. R. Kartha, C. H. Botting, R. A. Field, Org. Biomol. Chem. 2005, 3, 3468-3470.
-
(2005)
Org. Biomol. Chem
, vol.3
, pp. 3468-3470
-
-
Mukhopadhyay, B.1
Cura, P.2
Kartha, K.P.R.3
Botting, C.H.4
Field, R.A.5
-
152
-
-
0025708112
-
-
a) H. Kunz, S. Birnbach, P. Wernig, Carbohydr. Res. 1990, 202, 207-223;
-
(1990)
Carbohydr. Res
, vol.202
, pp. 207-223
-
-
Kunz, H.1
Birnbach, S.2
Wernig, P.3
-
153
-
-
0032501470
-
-
b) S. D. Kuduk, J. B. Schwarz, X.-T. Chen, P. W. Glunz, D. Sames, G. Ragupathi, P. O. Livingston, S. J. Danishefsky, J. Am. Chem. Soc. 1998, 120, 12474-12485;
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 12474-12485
-
-
Kuduk, S.D.1
Schwarz, J.B.2
Chen, X.-T.3
Glunz, P.W.4
Sames, D.5
Ragupathi, G.6
Livingston, P.O.7
Danishefsky, S.J.8
-
154
-
-
33646473587
-
-
c) N. Laurent, D. Lafont, P. Boullanger, Carbohydr. Res. 2006, 341, 823-835.
-
(2006)
Carbohydr. Res
, vol.341
, pp. 823-835
-
-
Laurent, N.1
Lafont, D.2
Boullanger, P.3
|