InCl3-induced C-glycosylation of per-O-acetylglycals with allyltrimethylsilane

被引:45
作者
Ghosh, R [1 ]
De, D
Shown, B
Maiti, SB
机构
[1] Jadavpur Univ, Dept Chem, Calcutta 700032, W Bengal, India
[2] Bangabasi Coll, Dept Chem, Calcutta 700009, W Bengal, India
关键词
InCl3; C-glycosylation; allyltrimethylsilane; glycal;
D O I
10.1016/S0008-6215(99)00219-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
InCl3 has been used for the first time as a mediator for the C-glycosylation of per-O-acetylglycals with allyltrimethylsilane, and the reactions proceeded to give products in good-to-excellent yield and in high diastereoselectivity. The 1,5-anti diastereoselectivity in the allylation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol and the 1,4-anti diastereoselectivity with 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-pent-1-enitol are in the range 80-90%, whereas 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol furnished exclusively the corresponding C-alpha-D-galactopyranosyl compound. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码:1 / 3
页数:3
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