Synthesis of 2,3-diazido-2,3-dideoxy-β-D-mannosides and 2,3-diazido-2,3-dideoxy-β-D-mannuronic acid via stereoselective anomeric O-alkylation

被引：0

作者：

Banjara, Rama ^{[1
,2
]}

Thapa, Prakash ^{[1
,2
]}

Kela, Shailja Hitesh ^{[1
,2
]}

Wu, Fenglang ^{[1
,2
]}

Zhu, Jianglong ^{[1
,2
]}

机构：

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

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

来源：

CARBOHYDRATE RESEARCH | 2024年 / 545卷

基金：

美国国家卫生研究院;

关键词：

Anomeric O -alkylation; beta-Mannoside; beta-Mannuronic acid; Bacterial polysaccharides; TRISACCHARIDE REPEATING-UNIT; CONTAINING GLYCAN CHAIN; POLYSACCHARIDE;

D O I：

10.1016/j.carres.2024.109279

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：

Stereoselective synthesis of 2,3-diazido-2,3-dideoxy-beta-d-mannosides has been accomplished via Cs2CO3-mediated anomeric O-alkylation of 2,3-diazido-2,3-dideoxy-beta-d-mannoses with primary electrophiles. Selective oxidation of the C6 primary alcohol of the 2,3-diazido-2,3-dideoxy-beta-d-mannoside successfully produced corresponding 2,3-diazido-2,3-dideoxy-beta-d-mannuronic acid.

引用

页数：7

共 2 条

[1] Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxy-β-D-mannopyranosyl Uronates
Walvoort, Marthe T. C.
Moggre, Gert-Jan
Lodder, Gerrit
Overkleeft, Herman S.
Codee, Jeroen D. C.
van der Marel, Gijsbert A.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) : 7301 - 7315
[2] 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
Bhetuwal, Bishwa Raj
Woodward, Justin
Li, Xiaohua
Zhu, Jianglong
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2017, 36 (4-6) : 162 - 172

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