用于在温和条件下合成线性六糖的二硫代乙酰基糖苷供体。

DISAL glycosyl donors for the synthesis of a linear hexasaccharide under mild conditions.

作者信息

Petersen Lars, Laursen Jane B, Larsen Kim, Motawia M Saddik, Jensen Knud J

机构信息

Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800 Kgs. Lyngby, Denmark.

出版信息

Org Lett. 2003 Apr 17;5(8):1309-12. doi: 10.1021/ol034242q.

DOI:10.1021/ol034242q

PMID:12688746

Abstract

[reaction: see text] The new class of glycosyl donors with a methyl 3,5-dinitrosalicylate (DISAL) anomeric leaving group has proved efficient for glycosylation under strictly neutral, mildly basic, or mildly acidic conditions. Here, we report the synthesis of novel DISAL disaccharide glycosyl donors prepared by easy nucleophilic aromatic substitution. These DISAL donors proved efficient in the synthesis of a starch-related hexasaccharide under very mild conditions. Glycosylations proceeded with alpha-selectivity and were compatible with Trt protecting groups.

摘要

[反应：见正文] 具有3,5-二硝基水杨酸甲酯（DISAL）异头离去基团的新型糖基供体已被证明在严格中性、弱碱性或弱酸性条件下进行糖基化反应时效率很高。在此，我们报道了通过简便的亲核芳香取代反应制备的新型DISAL二糖糖基供体的合成。这些DISAL供体在非常温和的条件下合成淀粉相关六糖时证明是有效的。糖基化反应具有α选择性，并且与Trt保护基团兼容。