-
5
-
-
0000936683
-
-
Müller, E., Ed.; Thieme Verlag, Stuttgart
-
Möller, F. Methoden der Organische Chemie (Houben-Weyl), 4th ed.; Müller, E., Ed.; Thieme Verlag, Stuttgart, 1957, vol. 11/1, p. 311-326.
-
(1957)
Methoden der Organische Chemie (Houben-Weyl), 4th Ed.
, vol.11
, Issue.1
, pp. 311-326
-
-
Möller, F.1
-
7
-
-
0016089632
-
-
Tritylated 2-aminoethanol was used many times for introduction of 2-aminoethoxy groups into target molecules, mainly oligonucleotides. It was prepared in the reaction of trityl, or trityl like, chloride or bromide with 2-aminoethanol. For example see: a) Billimoria, J.D., Owen, J.S., Scott, G.H. Chem.Phys.Lipids 1974, 12, 327-43; Chem.Abstr. 1975, 83, 131086u;
-
(1974)
Chem. Phys. Lipids
, vol.12
, pp. 327-43
-
-
Billimoria, J.D.1
Owen, J.S.2
Scott, G.H.3
-
8
-
-
0016089632
-
-
Tritylated 2-aminoethanol was used many times for introduction of 2-aminoethoxy groups into target molecules, mainly oligonucleotides. It was prepared in the reaction of trityl, or trityl like, chloride or bromide with 2-aminoethanol. For example see: a) Billimoria, J.D., Owen, J.S., Scott, G.H. Chem.Phys.Lipids 1974, 12, 327-43; Chem.Abstr. 1975, 83, 131086u;
-
(1975)
Chem. Abstr.
, vol.83
-
-
-
9
-
-
3242727483
-
-
b) Butskus, P.F., Sabonene, P.Yu., Lemeshene, D.B. Zh. Org. Khim. 1970, 6, 1984;
-
(1970)
Zh. Org. Khim.
, vol.6
, pp. 1984
-
-
Butskus, P.F.1
Sabonene, P.Yu.2
Lemeshene, D.B.3
-
10
-
-
0028231704
-
-
c) Kawakami, Junji; Uesugi, Seiichi; Ikehara, Morio; Itoh, Teiji; Miura, Kazunobu; Ohtsuka, Eiko Nucleosides Nucleotides 1994, 13, 421-428;
-
(1994)
Nucleosides Nucleotides
, vol.13
, pp. 421-428
-
-
Kawakami, J.1
Uesugi, S.2
Ikehara, M.3
Itoh, T.4
Miura, K.5
Ohtsuka, E.6
-
14
-
-
0034629431
-
-
g) Perlman, N., Livneh, M., Albeck, A., Tetrahedron 2000, 56; 1505-1516;
-
(2000)
Tetrahedron
, vol.56
, pp. 1505-1516
-
-
Perlman, N.1
Livneh, M.2
Albeck, A.3
-
15
-
-
3242684987
-
-
h) Tanaka, T., Tamatsukuri, S., Ikehara, M. Tetrahedron Lett. 1987, 28, 2611-2614;
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 2611-2614
-
-
Tanaka, T.1
Tamatsukuri, S.2
Ikehara, M.3
-
16
-
-
0023897333
-
-
i) Tanaka, T., Yamada, Y., Ikehara, M. Chem. Pharm. Bull. 1988, 36; 1386-1392;
-
(1988)
Chem. Pharm. Bull.
, vol.36
, pp. 1386-1392
-
-
Tanaka, T.1
Yamada, Y.2
Ikehara, M.3
-
19
-
-
0026760304
-
-
The reaction of tritylation of 2-aminoethanol was investigated in details by Butskus (ref. 4b) and Koermendy (Ref. 4d). There is only one example of tritylation of β-aminoalcohol other than 2-aminoethanol, described in: l) Bol, K.M., Liskamp, R.M.J. Tetrahedron Lett. 1991, 32, 5401-5404; l) Bol, K.M., Liskamp, R.M.J. Tetrahedron 1992, 48, 6425-6438.
-
(1992)
Tetrahedron
, vol.48
, pp. 6425-6438
-
-
Bol, K.M.1
Liskamp, R.M.J.2
-
21
-
-
0035854292
-
-
In fact, we have found only one paper in which the reaction of 4-chlorophenylglycidyl ether with tritylamine was described, see: Desai, R.C. J. Org. Chem. 2001, 66, 4939-4940.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 4939-4940
-
-
Desai, R.C.1
-
22
-
-
3242735537
-
-
note
-
We have previously checked several solvents and found methanol to be superior over any other solvent. Isopropanol - a common solvent for epoxide ring opening reaction gave rather low yields of the desired product.
-
-
-
-
27
-
-
33751498927
-
-
e) Chini, M., Crotti, P., Macchia, F. J. Org. Chem. 1991, 56, 5939-5942;
-
(1991)
J. Org. Chem.
, vol.56
, pp. 5939-5942
-
-
Chini, M.1
Crotti, P.2
Macchia, F.3
-
28
-
-
0025277198
-
-
f) Chini, M., Crotti, P., Macchia, F. Tetrahedron Lett. 1990, 31, 4661-4664;
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 4661-4664
-
-
Chini, M.1
Crotti, P.2
Macchia, F.3
-
30
-
-
0000387957
-
-
h) Padwa, A., Chen, Y., Chiacchio, U., Dent, W. Tetrahedron 1985, 41, 3529-3535;
-
(1985)
Tetrahedron
, vol.41
, pp. 3529-3535
-
-
Padwa, A.1
Chen, Y.2
Chiacchio, U.3
Dent, W.4
-
32
-
-
0033979286
-
-
j) Rampalli, S., Chaudhari, S.S., Akamanchi, K.G. Synthesis 2000, 78-80;
-
(2000)
Synthesis
, pp. 78-80
-
-
Rampalli, S.1
Chaudhari, S.S.2
Akamanchi, K.G.3
-
33
-
-
0030715003
-
-
k) Remuzon, P., Soumeillant, M., Dussy, C., Bouzard, D. Tetrahedron 1997, 53, 17711-17726;
-
(1997)
Tetrahedron
, vol.53
, pp. 17711-17726
-
-
Remuzon, P.1
Soumeillant, M.2
Dussy, C.3
Bouzard, D.4
-
34
-
-
0005121519
-
-
l) Stolberg, M.A., O'Neill, J.J., Wagner-Jauregg, T. J. Amer. Chem. Soc. 1953, 75, 5045;
-
(1953)
J. Amer. Chem. Soc.
, vol.75
, pp. 5045
-
-
Stolberg, M.A.1
O'Neill, J.J.2
Wagner-Jauregg, T.3
-
37
-
-
0000094270
-
-
o) Yamada, J., Yumoto, M., Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255-4258;
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 4255-4258
-
-
Yamada, J.1
Yumoto, M.2
Yamamoto, Y.3
-
38
-
-
37049082911
-
-
p) Yamamoto, Y., Asao, N., Meguro, M., Tsukada, N., Nemoto, H., Sadayori, N., Wilson, J.G., Nakamura, H. J. Chem. Soc. Chem. Commun. 1993, 15, 1201-1203.
-
(1993)
J. Chem. Soc. Chem. Commun.
, vol.15
, pp. 1201-1203
-
-
Yamamoto, Y.1
Asao, N.2
Meguro, M.3
Tsukada, N.4
Nemoto, H.5
Sadayori, N.6
Wilson, J.G.7
Nakamura, H.8
-
39
-
-
0019812208
-
-
For example: a) Acheson, R.M., Bite, M.G., Kemp, J.E.G. J.Med.Chem. 1981, 24, 1300-1304;
-
(1981)
J. Med. Chem.
, vol.24
, pp. 1300-1304
-
-
Acheson, R.M.1
Bite, M.G.2
Kemp, J.E.G.3
-
40
-
-
0031181243
-
-
b) Filipek, B., Sapa, J., Malawska, B., Kulig, K., Antkiewicz-Michaluk, L. Arch. Pharm. (Weinheim) 1997, 330, 225-232;
-
(1997)
Arch. Pharm. (Weinheim)
, vol.330
, pp. 225-232
-
-
Filipek, B.1
Sapa, J.2
Malawska, B.3
Kulig, K.4
Antkiewicz-Michaluk, L.5
-
41
-
-
0026078640
-
-
c) Hoefle, M.L., Blouin, L.T., Fleming, R.W., Hastings, S., Hinkley, J.M., Mertz, T.E., Steffe, T.J., Stratton, C.S., Werbel, R.M. J. Med. Chem. 1991, 34, 7-12;
-
(1991)
J. Med. Chem.
, vol.34
, pp. 7-12
-
-
Hoefle, M.L.1
Blouin, L.T.2
Fleming, R.W.3
Hastings, S.4
Hinkley, J.M.5
Mertz, T.E.6
Steffe, T.J.7
Stratton, C.S.8
Werbel, R.M.9
-
42
-
-
3242673168
-
-
d) Protiva, M., Sustr, M., Borovička, M. Chem. Listy 1951, 45, 43-4; Chem. Abstr. 1951, 45, 9010e.
-
(1951)
Chem. Listy
, vol.45
, pp. 43-4
-
-
Protiva, M.1
Sustr, M.2
Borovička, M.3
-
43
-
-
25944465098
-
-
d) Protiva, M., Sustr, M., Borovička, M. Chem. Listy 1951, 45, 43-4; Chem. Abstr. 1951, 45, 9010e.
-
(1951)
Chem. Abstr.
, vol.45
-
-
-
44
-
-
3242738196
-
-
note
-
The crude product contains some polymeric fraction which could be removed by recrystallization from dioxane/water.
-
-
-
-
45
-
-
3242726639
-
-
note
-
Because its steric hindrance and high symmetry, the trityl group is dominating over the rest of molecule. This effect increases the melting points of all tritylated products and makes crystallization easy, so the trityl group is really the "crystal maker".
-
-
-
-
46
-
-
3242716604
-
-
note
-
The regioselectivity of the ring opening of propylene and butylene oxide is usually ignored in published papers. Authors believed that ring opening is giving always "beta" products.
-
-
-
-
47
-
-
3242669550
-
-
It is worth to note that even before introduction of modern NMR instruments into organic labs, it was possible to determine the ratio of ring opening products just by recrystallization of the N-benzoyl derivatives of both aminoalcohols, for example, in the reaction of styrene oxide and ammonia. See: Castro, A.J., Brain, D.K., Fisher, H.D., Fuller, R.K. J. Org. Chem. 1954, 19, 1444.
-
(1954)
J. Org. Chem.
, vol.19
, pp. 1444
-
-
Castro, A.J.1
Brain, D.K.2
Fisher, H.D.3
Fuller, R.K.4
-
48
-
-
3242741760
-
-
note
-
The 1-phenyl-2-(triphenylmethylamino)ethanol was hydrolyzed 15 minutes in 2M hydrochloric acid, since concentrated hydrochloric acid gave also about 30% (molar) of the 2-chloro-2-phenylethyl(triphenylmethyl)amine which could be converted to the 2-amino-1-phenylethanol by increasing the time of hydrolysis. This chemistry, related to hydramine fission, is under investigation.
-
-
-
|