Synthesis of persialylated β-cyclodextrins

被引：45

作者：

Roy, R ^{[1
]}

Hernández-Mateo, F ^{[1
]}

Santoyo-González, F ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 25期

关键词：

D O I：

10.1021/jo005616l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of homogeneous hepta-antennated C-6 branched sialosyl cyclomaltoheptose derivatives (persialylated beta -cyclodextrins) has been performed in good to excellent yields, and the compounds have been fully characterized. The thioacetate N-acetylneuraminic acid derivative 6 was selectively de-S-acetylated and coupled by nucleophilic displacement in a one-pot reaction to the heptakis(chloroacetamido) beta -CDs 2 and 5, yielding multivalent sialosides 8 and 9 respectively. The thiourea-linked sialyl-CD 10 was obtained by reaction of the 4 -isothiocyanatophenyl N-acetylneuraminic acid derivative 7 with the per-tert-butoxycarbonylamino beta -CD derivative 2 after suitable deprotection of the amino function.

引用

页码：8743 / 8746

页数：4

共 45 条

[21] CARBOHYDRATE-PROTEIN INTERACTIONS - BASIS OF GLYCOBIOLOGY [J].