A convenient route to O-glycosyl lactates via conjugate addition to 2-nitro-glycals:: Ring closure to novel pyrano[2.3-b][1,4]-oxazines

被引：21

作者：

Khodair, AI

Pachamuthu, K

Schmidt, RR

机构：

[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

[2] Tanta Univ, Fac Educ, Dept Chem, Kafr El Sheikh Branch, Kafr Al Sheikh, Egypt

来源：

SYNTHESIS-STUTTGART | 2004年 / 01期

关键词：

glycal; nitroolefin; Michael additions; glycosides; peptide mimetic; bicyclic systems; azadioxadecalines;

D O I：

10.1055/s-2003-42494

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lactate esters D-2a, L-2a, and D-2b could be readily added to 3,4,6-tri-O-benzyl-2-nitro-galactal (1) and 3,4,6-tri-O-benzyl-2-nitro-glucal (4), affording exclusively alpha- and beta-anomers with galacto- and gluco-configuration, respectively. Nitro group reduction to the amino group and ester cleavage led to compounds 6a, 6b, and 7, which can be regarded as dipeptide mimetics. For these compounds the bicyclic pyrano[2.3-b][1,4]-oxazines 8-10 were prepared via ring closure.

引用

页码：53 / 58

页数：6

共 21 条

[1] ADDITION OF HALOGENOAZIDES TO GLYCALS [J].