Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses

被引：3

作者：

Bayer, Marius ^{[1
]}

Maichle-Moessmer, Caecilia ^{[1
]}

Ziegler, Thomas ^{[1
]}

机构：

[1] Univ Tubingen, Inst Organ Chem, Morgenstelle 18, D-72076 Tubingen, Germany

来源：

MOLBANK | 2020年 / 2020卷 / 01期

关键词：

oxetane; epoxide; rearrangement; carbohydrate; C-glycosylation; spiro-oxetane; ester group migration; STEREOSELECTIVE-SYNTHESIS; KETOOXETANES; GLYCALS; RING;

D O I：

10.3390/M1108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation of the pure epoxide was not possible since a rapid reversible conversion accompanied by the migration of the ester group took place and resulted in the formation of an unusual oxetane-bridged disaccharide scaffold. X-ray diffractometric structure elucidation and the suggested mechanism of the rearrangement are provided.

引用

页数：9

共 19 条

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