BRANCHED-CHAIR SUGARS .14. SYNTHESIS OF EVERNITROSE AND 3-EPI-EVERNITROSE

被引:41
作者
YOSHIMURA, J
MATSUZAWA, M
SATO, KI
NAGASAWA, Y
机构
[1] Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology, Midori-ku, Yokohama, 227, Nagatsuta
关键词
D O I
10.1016/0008-6215(79)80007-5
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
Evernitrose (2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-arabino-hexopyranose) was synthesized from methyl 2,6-dideoxy-4-O-methyl-α-L-erythro-hexopyranosid-3-ulose (2) through introduction of an amino group attached to the tertiary branching carbon by the method of Bourgeois, and subsequent oxidation of the amino group by m-chloroperoxybenzoic acid to a nitro group. 3-Cyano-3-O-mesylation of 2 by Bourgeois's method gave exclusively the desired product having the L-ribo configuration; furthermore, the β anomer of 2 gave the L-ribo and L-arabino products in the ratio of 1:2. The latter compound was converted into 3-epi-evernitrose by a similar sequence of reactions. © 1979.
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页码:67 / 78
页数:12
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