SYNTHESIS OF 6-O-(ALPHA-D-MANNOPYRANOSYL)-D-MYO-INOSITOL - A FRAGMENT FROM MYCOBACTERIA PHOSPHOLIPIDS

被引：54

作者：

ELIE, CJJ ^{[1
]}

VERDUYN, R ^{[1
]}

DREEF, CE ^{[1
]}

BROUNTS, DM ^{[1
]}

VANDERMAREL, GA ^{[1
]}

VANBOOM, JH ^{[1
]}

机构：

[1] GORLAEUS LABS,POB 9502,2300 RA LEIDEN,NETHERLANDS

来源：

TETRAHEDRON | 1990年 / 46卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)81480-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride (12) or ethyl 2-O- benzoyl-3,4,6-tri-0-benzyl-1-thio-α-D-mannopyranoside (13) with racemic 1,2-0-cyclohexylidene-3,4,5 tri-O-benzyl- myo-inositol (11) gave, after deacylation and column chromatography, the enantiomorphs 16a and 16b. Benzylation, acid hydrolysis of the 1,2-O-cyclohexylidene group and regioselective allylation of 16b led to 4b, which was deblocked by deallylation and hydrogenolysis to give 6-O-(α-O-D-mannopyranosyl)-D-myo-inositol (5b). Any attempt to glycosylate the hydroxyl at the axial C-2 position of the myo-inositol moiety in 4b with the mannopyranosyl fluoride 12 or the ethyl thiomannopyranoside 13 failed. © 1990.

引用

页码：8243 / 8254

页数：12

共 33 条

[11] STEREOSELECTIVE GLYCOSYLATION OF ALCOHOLS AND SILYL ETHERS USING GLYCOSYL FLUORIDES AND BORON-TRIFLUORIDE ETHERATE [J].