Synthesis of anomeric sulfur analogues of CMP-Neu5Ac containing tethered alkane or arene

被引：4

作者：

Chang, KH ^{[1
]}

Tao, YS ^{[1
]}

Li, WS ^{[1
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan

来源：

SYNLETT | 2004年 / 01期

关键词：

sialylation; hydroxyalkyl (aryl) thioglycosides; selective deprotection; sialyltransferase;

D O I：

10.1055/s-2003-43349

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to the synthesis of anomeric sulfur analogues of CMP-Neu5Ac containing alkane or arene linkage 1a-d is described. The procedure involves the high beta-stereoselectivity in sialylation of the peracetylated sialic acid methyl ester 4 with mercaptoalkyl (aryl) trichloroacetate 5a-d, followed by selective deprotection of the trichloroacetyl group to the corresponding hydroxyalkyl and hydroxyaryl thioglycosides 2a-d. Subsequent O-phosphitylation of 2a-d with respective 3a or 3c, followed by oxidation and deprotection led to the isolation of the target compounds 1a-d in good yields.

引用

页码：37 / 40

页数：4

共 36 条

[21]

Rosenberg A., 1995, BIOL SIALIC ACIDS

[22] SYNTHESIS AND ENZYMATIC AND NMR-STUDIES OF NOVEL SIALOSIDE PROBES - UNPRECEDENTED, SELECTIVE NEURAMINIDASE HYDROLYSIS OF AND INHIBITION BY C-6-(METHYL)-GAL SIALOSIDES [J].