Acid-catalysed rearrangement of glycosyl trichloroacetimidates: a novel route to glycosylamines

被引：12
|
作者：
Larsen, Kim [1 ,2 ]
Olsen, Carl Erik [1 ,3 ]
Motawia, Mohammed Saddik [1 ]
机构：
[1] Univ Copenhagen, Fac Life Sci, Dept Plant Biol, Plant Biochem Lab,Ctr Mol Plant Physiol, DK-1871 Copenhagen, Denmark
[2] Glostrup Cty Hosp, Dept Clin Biochem, Glostrup Res Inst, DK-2600 Glostrup, Denmark
[3] Univ Copenhagen, Fac Life Sci, Dept Nat Sci, DK-1871 Copenhagen, Denmark
来源：
CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 02期
关键词：
chapman rearrangement; glycosylamine; reduction; trichloroacetimidate; ASPARAGINE-LINKED GLYCOSYLATION; INTERMOLECULAR AGLYCON TRANSFER; IMINO-ARYL ETHERS; CHEMICAL-SYNTHESIS; PROTECTING GROUPS; AZIDES; SUGAR; OLIGOSACCHARIDES; GLYCOBIOLOGY; INTERMEDIATE;
D O I：
10.1016/j.carres.2007.10.019
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：
A novel route to glycosylamines has been developed. Treatment of glycosyl trichloroacetimidates with TMSOTf under glycosylation conditions, but in the absence of an acceptor, resulted in complete rearrangement of the trichloroacetimidates into the corresponding N-protected-glycosylamines. Reductive cleavage of the trichloroacetyl groups using sodium borohydride provided the desired glycosylamine products. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：383 / 387
页数：5
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