Polyhydroxylated pyrrolidines. Part 2: Highly stereoselective synthesis of partially protected DMDP derivatives from D-fructose

被引：32

作者：

Izquierdo, I ^{[1
]}

Plaza, MT ^{[1
]}

Franco, F ^{[1
]}

机构：

[1] Univ Granada, Fac Pharm, Dept Med & Organ Chem, Granada 18071, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(02)00369-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The readily available 3,4-di-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranose 2 was straightforwardly transformed into 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-beta-D-fructopyranose 4, after treatment under modified Garegg's conditions followed by reaction of the resulting 3,4-di-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-L-sorbopyranose 3 with sodium azide in DMF. Cleavage of the acetonide of 4 to afford 6 followed by regioselective O-tert-butyldiphenylsilylation at C(1)OH afforded 7. Hydrogenation of 7 proceeded with high stereoselectivity yielding 3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-D-mannitol 1, confirmed by its O-desilylation to 8. Compound 1 was subjected to different N-protection reactions to afford the corresponding N-allyl (1a), N-benzyl (1b), and N-tert-butyloxycarbonyl (1c) derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1503 / 1508

页数：6

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