Tunable activation of glycosyl trichloro- and (N-phenyl)trifluoroacetimidates with ytterbium(III) triflate:: One-pot synthesis of trisaccharides under catalytic conditions

被引：26

作者：

Adinolfi, M ^{[1
]}

Iadonisi, A ^{[1
]}

Ravidà, A ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

来源：

SYNLETT | 2006年 / 04期

关键词：

carbohydrates; glycosidations; ytterbium(III) triflate; solvent effects; stereoselectivity;

D O I：

10.1055/s-2006-932484

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild promoter such as Yb(OTf)(3) allows selective activation of glycosyl trichloroacetimidate building blocks in the presence of glycosyl (N-phenyl)trifluoroacetimidates with a similar pattern of protecting groups. This selectivity has been exploited in the one-pot assembly of two different trisaccharides in good overall yields. In contrast to other reported procedures, a catalytic amount of promoter is sufficient to trigger both glycosidation steps of the sequential process.

引用

页码：583 / 586

页数：4

共 7 条

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[6] ONE-POT SYNTHESIS OF PROPELLANE HETERO ANALOG FROM N-PHENYL-SUBSTITUTED 3-ACYL-1,2-DIHYDROCINNOLINE-1,2-DICARBOXIMIDES UNDER PHASE-TRANSFER-CATALYZED CONDITIONS
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