Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: The first enantiomer of a natural acetal glucoside

被引：17
作者：
Kluge, M
Schneider, B
Sicker, D
机构：
[1] UNIV LEIPZIG,INST ORGAN CHEM,D-04103 LEIPZIG,GERMANY
[2] INST PFLANZENBIOCHEM HALLE,D-06018 HALLE,GERMANY
来源：
CARBOHYDRATE RESEARCH | 1997年 / 298卷 / 03期
关键词：
acetal glucoside; benzoxazinone; glycosylation; stereoselective; hydroxamic acid GDIMBOA; enantiomer of; synthesis of;
D O I：
10.1016/S0008-6215(96)00303-5
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：
The synthesis of (2S)-2-beta-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, the enantiomer of the natural acetal glucoside GDIMBOA from maize, has been achieved by the double diastereoselective L-glucosylation of racemic 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one with 2,3,4,6-tetra-O-acetyl-beta-L-glucopyranosyl trichloroacetimidate in the presence of excess of boron trifluoride etherate as promoter as well as protecting and equilibrating agent. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：147 / 152
页数：6
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