A short synthesis of protected 3-deoxy-D-arabino-2-heptulosonates (DAH) from shikimic acid based on silyl group migration

被引：1

作者：

Gonda, Jozef ^{[1
]}

Psotka, Miroslav ^{[2
]}

Martinkova, Miroslava ^{[1
]}

Fazekasova, Simona ^{[1
]}

Mitrikova, Tatiana ^{[1
]}

Vilkova, Maria ^{[1
]}

机构：

[1] Safarik Univ, Dept Organ Chem, Moyzesova 11, Kosice 04001, Slovakia

[2] Univ Hosp Hradec Kralove, Biomed Res Ctr, Sokolska 581, Hradec Kralove 50005, Czech Republic

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 52期

关键词：

Oxoheptanals; Heptulosonates; Silyl group migration; Shikimic acid; PATHWAY ENZYMES; TARGETS;

D O I：

10.1016/j.tetlet.2018.11.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals with lower alcohols produced protected 3-deoxy-D-arabino-2-heptulosonates. The key transformation is based on an 1,4-O-O silyl group migration, followed by 6-exo-trig cyclisation to give the final pyranose. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：4620 / 4621

页数：2

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