-
1
-
-
33644926160
-
-
For pyrazofurin and formycin, see: a, Katritzky, A. R, Ed, Academic Press: San Diego
-
For pyrazofurin and formycin, see: (a) Shaban, M. A. E.; Nasr, A. Z. In Advances in Heterocyclic Chemistry, Vol. 68; Katritzky, A. R., Ed.; Academic Press: San Diego, 1997, 259.
-
(1997)
Advances in Heterocyclic Chemistry
, vol.68
, pp. 259
-
-
Shaban, M.A.E.1
Nasr, A.Z.2
-
2
-
-
33644931372
-
-
Katritzky, A. R, Ed, Academic Press: San Diego
-
(b) Shaban, M. A. E.; Nasr, A. Z. In Advances in Heterocyclic Chemistry, Vol. 70; Katritzky, A. R., Ed.; Academic Press: San Diego, 1998, 230.
-
(1998)
Advances in Heterocyclic Chemistry
, vol.70
, pp. 230
-
-
Shaban, M.A.E.1
Nasr, A.Z.2
-
3
-
-
78651158403
-
-
For showdomycin, see
-
(c) For showdomycin, see: Nishimura, H.; Mayama, M.; Komatsu, Y.; Kato, H.; Shimsoka, N.; Tanaka, Y. J. Antibiot., Ser. A 1964, 17, 148.
-
(1964)
J. Antibiot., Ser. A
, vol.17
, pp. 148
-
-
Nishimura, H.1
Mayama, M.2
Komatsu, Y.3
Kato, H.4
Shimsoka, N.5
Tanaka, Y.6
-
4
-
-
0018665617
-
-
(d) Rabinovitz, M.; Uehara, Y.; Vistica, D. T. Science 1979, 206, 1085.
-
(1979)
Science
, vol.206
, pp. 1085
-
-
Rabinovitz, M.1
Uehara, Y.2
Vistica, D.T.3
-
7
-
-
0031564957
-
-
For recent articles, see: For a review, see
-
(a) For recent articles, see: For a review, see: Maden, B. E. H. Nature (London) 1997, 389, 129.
-
(1997)
Nature (London)
, vol.389
, pp. 129
-
-
Maden, B.E.H.1
-
8
-
-
40749133304
-
-
(b) Chang, Y.-C.; Herath, J.; Wang, T. H.-H.; Chow, C. S. Bioorg. Med. Chem. 2008, 16, 2676.
-
(2008)
Bioorg. Med. Chem
, vol.16
, pp. 2676
-
-
Chang, Y.-C.1
Herath, J.2
Wang, T.H.-H.3
Chow, C.S.4
-
12
-
-
0037191631
-
-
(c) Guianvarc'h, D.; Fourrey, J.-L.; Maurisse, R.; Sun, J.-S.; Benhida, R. Org. Lett. 2002, 4, 4209.
-
(2002)
Org. Lett
, vol.4
, pp. 4209
-
-
Guianvarc'h, D.1
Fourrey, J.-L.2
Maurisse, R.3
Sun, J.-S.4
Benhida, R.5
-
13
-
-
0038143610
-
-
(d) Guianvarc'h, D.; Fourrey, J.-L.; Sun, J.-S.; Maurisse, R.; Benhida, R. Bioorg. Med. Chem. 2003, 11, 2751.
-
(2003)
Bioorg. Med. Chem
, vol.11
, pp. 2751
-
-
Guianvarc'h, D.1
Fourrey, J.-L.2
Sun, J.-S.3
Maurisse, R.4
Benhida, R.5
-
14
-
-
33746277587
-
-
(e) Leconte, A. M.; Matsuda, S.; Hwang, G. T.; Romesberg, F. E. Angew. Chem. Int. Ed. 2006, 45, 4326.
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 4326
-
-
Leconte, A.M.1
Matsuda, S.2
Hwang, G.T.3
Romesberg, F.E.4
-
15
-
-
3142736550
-
-
For recent reviews on the chemistry of C-glycoside analogues, see: (a) Wu, Q.; Simons, C. Synthesis 2004, 1533.
-
For recent reviews on the chemistry of C-glycoside analogues, see: (a) Wu, Q.; Simons, C. Synthesis 2004, 1533.
-
-
-
-
17
-
-
43449099607
-
-
For recent articles, see
-
(c) For recent articles, see: Wellington, K. W.; Benner, S. A. Nucleosides, Nucleotides Nucleic Acids 2005, 1309.
-
(2005)
Nucleosides, Nucleotides Nucleic Acids
, pp. 1309
-
-
Wellington, K.W.1
Benner, S.A.2
-
18
-
-
0037204699
-
-
(d) Guianvarc'h, D.; Fourrey, J.-L.; Tran Huu Dau, M.-E.; Guérineau, V.; Benhida, R. J. Org. Chem. 2002, 67, 3724.
-
(2002)
J. Org. Chem
, vol.67
, pp. 3724
-
-
Guianvarc'h, D.1
Fourrey, J.-L.2
Tran Huu Dau, M.-E.3
Guérineau, V.4
Benhida, R.5
-
19
-
-
33748994265
-
-
(e) Urban, M.; Pohl, R.; Klepetarova, B.; Hocek, M. J. Org. Chem. 2006, 71, 7322.
-
(2006)
J. Org. Chem
, vol.71
, pp. 7322
-
-
Urban, M.1
Pohl, R.2
Klepetarova, B.3
Hocek, M.4
-
20
-
-
34548742230
-
-
(f) Joubert, N.; Pohl, R.; Klepetarova, B.; Hocek, M. J. Org. Chem. 2007, 72, 6797.
-
(2007)
J. Org. Chem
, vol.72
, pp. 6797
-
-
Joubert, N.1
Pohl, R.2
Klepetarova, B.3
Hocek, M.4
-
21
-
-
0036828138
-
-
(a) Kodama, T.; Shuto, S.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2002, 67, 7706.
-
(2002)
J. Org. Chem
, vol.67
, pp. 7706
-
-
Kodama, T.1
Shuto, S.2
Ichikawa, S.3
Matsuda, A.4
-
22
-
-
1642299991
-
-
(b) Haraguchi, K.; Kubota, Y.; Tanaka, H. J. Org. Chem. 2004, 69, 1831.
-
(2004)
J. Org. Chem
, vol.69
, pp. 1831
-
-
Haraguchi, K.1
Kubota, Y.2
Tanaka, H.3
-
23
-
-
14544297394
-
-
(c) Ogamino, J.; Mizunuma, H.; Kumamoto, H.; Takeda, S.; Haraguchi, K.; Nakamura, K. T.; Sugiyama, H.; Tanaka, H. J. Org. Chem. 2005, 70, 1684.
-
(2005)
J. Org. Chem
, vol.70
, pp. 1684
-
-
Ogamino, J.1
Mizunuma, H.2
Kumamoto, H.3
Takeda, S.4
Haraguchi, K.5
Nakamura, K.T.6
Sugiyama, H.7
Tanaka, H.8
-
24
-
-
0035929187
-
-
(a) Guianvarc'h, D.; Benhida, R.; Fourrey, J.-L.; Maurisse, R.; Sun, J.-S. Chem. Commun. 2001, 1814.
-
(2001)
Chem. Commun
, pp. 1814
-
-
Guianvarc'h, D.1
Benhida, R.2
Fourrey, J.-L.3
Maurisse, R.4
Sun, J.-S.5
-
25
-
-
27944506869
-
-
(b) Peyron, C.; Benhida, R.; Bories, C.; Loiseau, P. Bioorg. Chem. 2005, 33, 439.
-
(2005)
Bioorg. Chem
, vol.33
, pp. 439
-
-
Peyron, C.1
Benhida, R.2
Bories, C.3
Loiseau, P.4
-
27
-
-
43449130076
-
-
(d) Spadafora, M.; Mehiri, M.; Burger, A.; Benhida, R. Tetrahedron Lett. 2008, 49, 3967.
-
(2008)
Tetrahedron Lett
, vol.49
, pp. 3967
-
-
Spadafora, M.1
Mehiri, M.2
Burger, A.3
Benhida, R.4
-
28
-
-
51149086603
-
-
Peyron, C.; Navarre, J. M.; Dubreuil, D.; Vierling, P.; Benhida, R. Tetrahedron Lett. 2008, 49, 6171.
-
(2008)
Tetrahedron Lett
, vol.49
, pp. 6171
-
-
Peyron, C.1
Navarre, J.M.2
Dubreuil, D.3
Vierling, P.4
Benhida, R.5
-
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62249164770
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2ah: 1H NMR (200 MHz, CDCl3, δ, 1.07-1.11 (2 x s, 9 H, Met-Bu, 1.30 (s, 3 H, Me, 1.48 (s, 3 H, Me, 3.72 (dd, 1 H, J, 3.6, 11.2 Hz, H5′, 3.90 (dd, 1 H, J, 3.5, 11.3 Hz, H5′, 4.36 (t, 1 H, J, 2.5 Hz, H4′, 4.62 (d, 1 H, J, 5.7 Hz, H 3′, 4.75 (s, 1 H, OH, 4.89 (dd, 1 H, J, 1.4, 5.6 Hz, H2′, 6.96 (s, 2 H, H3, H4, 7.37-7.46 (m, 6 H, Ph, 7.57-7.72 (m, 4 H, Ph, 13C NMR (50 MHz, CD 3OD, δ, 19.79 (CMe3, 24.44 (Me, 26.26 (Me, 26.51 (CMe3, 66.35 (C5′, 84.63 (C 2′, 87.19 (C4′ or C3′, 88.07 (C3′ or C4′, 106.85 (CMe2, 113.40 (C1′, 113.80 (C2, 126.15 (C4, 127.60 CPh
-
5SSi: C, 57.04; H, 5.64. Found: C, 57.17; H, 5.73.
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-
-
-
30
-
-
62249093517
-
-
2b: 1H NMR (200 MHz, CDCl3, CD 3OD, δ, 0.95 (s, 9 H, Met-Bu, 1.24 (s, 3 H, Me, 1.36 (s, 3 H, Me, 3.26-3.39 (m, 2 H, H5′, 3.62 (d, 1 H, J, 4.0 Hz, H4′, 4.26 (dd, 1 H, J, 6.8, 9.8 Hz, H 3′, 4.65 (d, 1 H, J, 6.8 Hz, H2′, 6.68 (d, 1 H, J, 3.9 Hz, H4, 6.76 (d, 1 H, J, 3.9 Hz, H3, 6.84 (d, 1 H, J, 3.8 Hz, H3, 7.05 (d, 1 H, J, 3.9 Hz, H4, 7.27-7.36 (m, 6 H, Ph, 7.45-7.62 (m, 4 H, Ph, 13C NMR (50 MHz, CDCl3, CD3OD, δ, 19.65 (CMe3, 24.14 (Me, 26.54 (Me, 27.14 (Me, t-Bu, 65.68 (C4′, 69.58 (C5′, 76.09 (C 3′, 77.63 (C1′, 83.83 (C2′, 109.32 (CMe2, 112.38-113.32 (C2, 125.54-125.60 C 4
-
+.
-
-
-
-
31
-
-
62249096640
-
-
K could be explained by the possible anisotropy of the TBDPS group (aryl-TBDPS π-stacking).
-
K could be explained by the possible anisotropy of the TBDPS group (aryl-TBDPS π-stacking).
-
-
-
-
32
-
-
62249116092
-
-
4ah: 1H NMR (200 MHz, CDCl3, δ, 1.07-1.12 (2 x s, 9 H, Met-Bu, 1.25 (s, 3 H, Me, 1.38 (s, 3 H, Me, 3.75 (dd, 1 H, J, 3.1, 11.2 Hz, H5′, 3.95 (dd, 1 H, J, 3.0, 11.5 Hz, H5′, 4.42-4.47 (m, 1 H, H 4′, 4.66 (d, 1 H, J, 5.7 Hz, H2′, 4.87-4.95 (m, 2 H, H3′, OH, 7.24-7.26 (m, 1 H, Ar, 7.37-7.71 (m, 13 H, Ph, Ar, 13C NMR (50 MHz, CDCl3, δ, 19.20 (CMe3, 24.87 (Me, 26.37 (Me, 26.92 (CMe3, 65.62 (C5′, 82.04 (C3′, 86.40 (C 4′, 88.36 (C2′, 106.60 (C 1′, 112.87 (CMe2, 121.82 (C3, 124.59 (CHAr, 127.84 (CPh, 129.15 (CHAr, 129.82 (CHAr, 130.19 (CPh, 130.39 (CHAr, 131.22 CPh, 135.62
-
+.
-
-
-
-
33
-
-
62249134859
-
-
7ah: 1H NMR (200 MHz, CDCl3, δ, 1.08-1.12 (2 x s, 9 H, Met-Bu, 1.26 (s, 3 H, Me, 1.40 (s, 3 H, Me, 3.71-4.01 (m, 5 H, H5′, OMe, 4.38-4.52 (m, 2 H, H 4′, OH, 4.63 (d, 1 H, J, 5.7 Hz, H2′, 4.92 (dd, 1 H, J, 1.5, 5.7 Hz, H3′, 6.89 (d, 2 H, J, 8.9 Hz, H3, 7.36-7.44 (m, 6 H, Ph, 7.54 (d, 2 H, J, 8.8 Hz, H2, 7.65-7.75 (m, 4 H, Ph, 13C NMR (50 MHz, CDCl3, δ, 19.39-19.49 (CMe3, 25.14-25.20 (Me, 26.71-26.82 (Me, 27.04-27.11 (CMe3, 55.38 (OMe, 65.88 (C5′, 82.23-82.33 (C3′, 86.43-86.54 (C 4′, 88.25 (C2′, 107.30 (C 1′, 112.84 (CMe2, 113.12 (C3, 128.08-128.13 (CPh, 128.44 (C2, 130.19-130.35 (C Ph, 131.60 C
-
k.
-
-
-
-
34
-
-
62249104892
-
-
2c: 1H NMR (200 MHz, CDCl3, δ, 1.05 (s, 9 H, Met-Bu, 1.29 (s, 3 H, Me, 1.39 (s, 3 H, Me, 3.70-4.12 (m, 3 H, H4′, H5′, 4.76 (dd, 1 H, J, 2.9, 5.9 Hz, H3′, 5.01 (d, 1 H, J, 5.8 Hz, H 2′, 6.41 (d, 1 H, J, 3.8 Hz, H4, 6.83 (d, 1 H, J, 3.9 Hz, H3, 6.87 (d, 1 H, J, 3.9 Hz, H 3, 6.98 (d, 1 H, J, 3.8 Hz, H4, 7.32-7.45 (m, 6 H, Ph, 7.65-7.78 (m, 4 H, Ph, 13C NMR (50 MHz, CDCl3, δ, 19.38 (CMe3, 24.68 (Me, 25.77 (Me, 26.94 (CMe 3, 61.83 (C5′, 77.36, 78.88, 80.43, 81.37 (C 4′, C3′, C1′, C 2′, 112.38-113.32 (C2, 113.36 (CMe2, 126.13-126.27 (C4, 127.74-127.81 (CPh, 128.83-129.79 C3, 133
-
2), 7.58-7.69 (m, 4 H, Ph).
-
-
-
-
35
-
-
62249184931
-
-
2d: mp 181-182°C. 1H NMR (200 MHz, CDCl3, CD3OD, δ, 3.47 (dd, 1 H, J, 2.8, 9.6 Hz, H 5′, 3.69 (dd, 1 H, J, 2.7, 7.9 Hz, H 5′, 3.82-3.96 (m, 2 H, H3′, H 4′, 4.49 (d, 1 H, J, 2.8 Hz, H2′, 6.54 (d, 1 H, J, 3.9 Hz, HTh, 6.87 (d, 1 H, J, 3.9 Hz, HTh, 7.01-7.08 (m, 2 H, HTh, 13C NMR (50 MHz, CDCl3, CD3OD, δ, 62.47 (C 5′, 71.33 (C3′, 80.42 (C4′, 82.65 (C2′, 88.64 (C1′, 112.09-112.18 (C2, 125.67-126.22 (C4, 128.26-129.30 (C3, 140.58-141.82 (C5, MS (ESI, m/z, 476.5, 478.5, 480.5 49, 100, 54, M, Na, Anal. Calcd for C13H 12Br2O4
-
6: C, 65.88; H, 6.40. Found: C, 66.03; H, 6.29.
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