Highly Stereoselective and Iterative Synthesis of α-(1→4)-Linked Polysaccharides Composed of 3-O-Methyl-d-mannose

A second-generation synthesis of synthetic 3-O-methyl-d-mannose-containing polysaccharides (sMMPs) is reported. The glycosidation of donor B and acceptor C, prepared from a common precursor A in two and one steps, respectively, is effected by t-butyldimethylsilyl trifluoromethanesulfonate to furnish...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 17; pp. 3323 - 3326
Main Authors Cheon, Hwan-Sung, Lian, Yiqian, Kishi, Yoshito
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.08.2007
Amer Chemical Soc
Subjects
Carbohydrate Conformation
Carbohydrate Sequence
Chemistry
Chemistry, Organic
Glycosylation
Methylmannosides - chemistry
Physical Sciences
Polysaccharides - chemical synthesis
Science & Technology
SILVER PERCHLORATE
GLOBO-H
REVISED STRUCTURE
DESIGN
GLUCOSE
GLYCOSYL PHOSPHATES
MYCOBACTERIUM-SMEGMATIS
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Summary:A second-generation synthesis of synthetic 3-O-methyl-d-mannose-containing polysaccharides (sMMPs) is reported. The glycosidation of donor B and acceptor C, prepared from a common precursor A in two and one steps, respectively, is effected by t-butyldimethylsilyl trifluoromethanesulfonate to furnish only the desired α-anomer D in high yields. Unlike the first-generation synthesis, this synthesis gives the desired product free from contamination of scrambling products. A three-step protocol is used to deprotect D to furnish sMMPs.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0713335