Direct anomeric O-arylation and O-hetarylation of glucose - Electron deficient aromatic and hetaromatic compounds in aryl and hetaryl glycoside synthesis

被引：17

作者：

Huchel, U ^{[1
]}

Schmidt, C ^{[1
]}

Schmidt, RR ^{[1
]}

机构：

[1] UNIV KONSTANZ,FAK CHEM,D-78434 CONSTANCE,GERMANY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 52期

关键词：

D O I：

10.1016/0040-4039(95)02034-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Anomeric O-arylation and O-hetarylation of tetra-O-benzyl-, tetra-O-acetyl-, and O-unprotected glucose (la-c) can be directly performed with electron deficient aromatic and heteroaromatic systems having fluoro- (2A-2F) or phenylsulfonyl (3B, 3G-3K), respectively, as leaving groups, The reactions were carried out in DMF as solvent at room temperature with NaH as the base; they led in the products 4 to an exchange of the leaving group by the glucopyranosyloxy moiety; mainly beta-products were obtained.

引用

页码：9457 / 9460

页数：4

共 24 条

[1] KINETICS OF REACTIONS IN HETEROCYCLES .11. REACTIONS OF 2-CHLORO-7-METHYLPURINES, 6-CHLORO-7-METHYLPURINES, AND 8-CHLORO-7-METHYLPURINES AND 2-METHYLSULPHONYL-7(9)-METHYLPURINES, 6-METHYLSULPHONYL-7(9)-METHYLPURINES, AND 8-METHYLSULPHONYL-7(9)-METHYLPURINES WITH HYDROXIDE IONS [J].