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ref 4
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For preliminary communications, see: (a) Jirousek, M. R.; Gillig, J. R.; Neel, D. A.; Rito, C. J.; O'Bannon, D.; Heath, W. F.; McDonald, J. H. III.; Faul, M. M.; Winneroski, L. L.; Melikian-Badalian, A.; Baevsky, M.; Ballas, L. M.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2093. (b) ref 4.
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22
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7144263367
-
-
note
-
(R)-(+)-Glycidol (16.) was purchased in 89% enantioselectivity from Diasco.
-
-
-
-
23
-
-
7144266623
-
-
note
-
(R)-1-Chloro-2,3-propanediol (21) was purchased in >98% enantioselectivity from Diasco.
-
-
-
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26
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0012447689
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0001606689
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(d) For a review, see: Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005.
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Binkley, R. W.; Ambrose, M. G.; Hehemann, D. G. J. Org. Chem. 1980, 45, 4387.
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0026540135
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(c) Achmatowicz, B.; Kabat, M. M., Krajewski, J.; Wicha, J. Tetrahedron 1992, 48, 10201.
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-
41
-
-
7144249507
-
-
note
-
On large scale yield of 7 by crystallization from DMF/acetonitrile varied from 55 to 68%.
-
-
-
-
43
-
-
84986458682
-
-
Bocchi, V.; Casnati, G.; Dossena, A.; Villani, F. Synthesis 1976, 414.
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Synthesis
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Bocchi, V.1
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-
45
-
-
7144224180
-
-
note
-
Neutralization with strong acid was unsuccessful due to competitive detritylation.
-
-
-
-
47
-
-
7144267560
-
-
A number of methods to deprotect imide nitrogens have been reported: (a) PMB (i) Akiyama, T.; Kumegawa, M.; Takesue, Y.; Nishimoto, H.; Ozaki, S. Chemistry Lett. 1990, 339. (ii) Van Aerschot, A.; Jie, L.; Herdewijn, P. Tetrahedron Lett. 1991, 32, 1905. (b) BOM: Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
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Akiyama, T.1
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Nishimoto, H.4
Ozaki, S.5
-
48
-
-
0025974997
-
-
A number of methods to deprotect imide nitrogens have been reported: (a) PMB (i) Akiyama, T.; Kumegawa, M.; Takesue, Y.; Nishimoto, H.; Ozaki, S. Chemistry Lett. 1990, 339. (ii) Van Aerschot, A.; Jie, L.; Herdewijn, P. Tetrahedron Lett. 1991, 32, 1905. (b) BOM: Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
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(1991)
Tetrahedron Lett.
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-
-
Van Aerschot, A.1
Jie, L.2
Herdewijn, P.3
-
49
-
-
0028789416
-
-
A number of methods to deprotect imide nitrogens have been reported: (a) PMB (i) Akiyama, T.; Kumegawa, M.; Takesue, Y.; Nishimoto, H.; Ozaki, S. Chemistry Lett. 1990, 339. (ii) Van Aerschot, A.; Jie, L.; Herdewijn, P. Tetrahedron Lett. 1991, 32, 1905. (b) BOM: Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
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J. Am. Chem. Soc.
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Link, J.T.1
Raghavan, S.2
Danishefsky, S.J.3
-
50
-
-
7144236591
-
-
note
-
-1, indicating that no cyclic imide was present.
-
-
-
-
51
-
-
85099487569
-
-
note
-
R = 8.0 min.
-
-
-
-
52
-
-
85099487796
-
-
note
-
R = 19.9 min.
-
-
-
-
53
-
-
85099487480
-
-
note
-
R = 22.7 min.
-
-
-
|