A new and concise synthesis of 3-deoxy-D-arabino-2-heptulopyranosonic acid (DAH) and derivatives through the radical chemistry of Barton esters

被引：16

作者：

Barton, DHR ^{[1
]}

Liu, WS ^{[1
]}

机构：

[1] TEXAS A&M UNIV,DEPT CHEM,COLLEGE STN,TX 77843

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 03期

关键词：

D O I：

10.1016/S0040-4039(96)02331-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Barton ester-based radical chemistry was applied in the synthesis of 3-deoxy-D-orobino-2-heptulopyranosonic acid (DAH) from commercial D-ribonolactone, The radical reaction with olefin 2, followed by aqueous work-up, provided the seven-carbon sugar compounds 5 and 6 (3:1) in 60% yield. Removal of the isopropylidene groups from 5 and hydrolysis of the ethyl ester yielded the DAH barium salt quantitatively. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：367 / 370

页数：4

共 26 条

[1]

[Anonymous], BIOSYNTHESIS AROMATI

[2]

[Anonymous], [No title captured]

[3] THE USE OF ASPERGILLUS-TERREUS EXTRACTS IN THE PREPARATIVE SYNTHESIS OF 2-KETO-3-DEOXY-ULOSONIC ACIDS [J].