Stereoselective -mannosylation via anomeric O-Alkylation: Concise synthesis of -D-Xyl-(l2)--D-Man-(14)--D-Glc-OMe, a trisaccharide oligomer of the hyriopsis schlegelii glycosphingolipid

被引：9

作者：

Bhetuwal, Bishwa Raj ^{[1
,2
]}

Woodward, Justin ^{[3
]}

Li, Xiaohua ^{[3
]}

Zhu, Jianglong ^{[1
,2
]}

机构：

[1] Univ Toledo, Dept Chem & Biochem, 2801 W Bancroft St, Toledo, OH 43606 USA

[2] Univ Toledo, Sch Green Chem & Engn, 2801 W Bancroft St, Toledo, OH 43606 USA

[3] Univ Michigan, Dept Nat Sci, 4901 Evergreen Rd, Dearborn, MI 48128 USA

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2017年 / 36卷 / 4-6期

基金：

美国国家科学基金会;

关键词：

-mannosylation; lactol; anomeric O-alkylation; glycosylation; INTRAMOLECULAR AGLYCON DELIVERY; BETA-D-MANNOPYRANOSIDES; TEMPORARY SILICON CONNECTION; GLYCOSIDE SYNTHESIS; DISACCHARIDES; OLIGOSACCHARIDES; GLYCOSYLATION; MANNOSIDES; ALPHA; CONSTRUCTION;

D O I：

10.1080/07328303.2017.1390579

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Synthesis of -D-Xyl-(l2)--D-Man-(14)--D-Glc-OMe (1), a tr-isaccharide oligomer of the Hyriopsis schlegelii glycosphingolipid is described. The synthesis involves a key -mannosylation via cesium carbonate-mediated anomeric O-alkylation for direct synthesis of partially protected disaccharide -D-Man-(14)--D-Glc-OMe (4) bearing a free C2OH in the mannose moiety. In addition, a silver triflate-promoted glycosylation of 4 with 2,3,4-tri-O-benzoyl--D-xylopyranosyl bromide (5) followed by deprotection affords the desired trisaccharide component (1) of the Hyriopsis schlegelii glycosphingolipid.

引用

页码：162 / 172

页数：11

共 59 条

[1] PREPARATION OF DISACCHARIDES HAVING A BETA-D-MANNOPYRANOSYL GROUP FROM N-PHTHALOYLLACTOSAMINE DERIVATIVES BY DOUBLE OR TRIPLE SN2 SUBSTITUTION [J].