The synthesis of 2-deoxy-α-d-glycosides from d-glycals catalyzed by TMSI and PPh3

2-Deoxyglycosides were synthesized in high α-selectivity by the direct addition of alcohols to d-glucal and d-galactal catalyzed by TMSI and PPh3. The acid labile isopropylidene group is tolerated under this condition.

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Bibliographic Details
Published inCarbohydrate research Vol. 358; pp. 19 - 22
Main Authors Cui, Xi-Kai, Zhong, Ming, Meng, Xiang-Bao, Li, Zhong-Jun
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.09.2012
Elsevier
Subjects
2-Deoxyglycoside
Biochemistry & Molecular Biology
Catalysis
Chemistry
Chemistry, Applied
Chemistry, Organic
Deoxy Sugars - chemical synthesis
Deoxy Sugars - chemistry
Deoxyglucose - analogs & derivatives
Deoxyglucose - chemistry
Glycal
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosylation
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Physical Sciences
Science & Technology
TMSI
Trimethylsilyl Compounds - chemistry
α-Selective glycosylation
Glycal
TMSI
2-Deoxyglycoside
α-Selective glycosylation
ALCOHOLS
alpha-Selective glycosylation
TETRAHYDROPYRANYLATION
2-DEOXY-ALPHA-GLYCOSIDES
MECHANISMS
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Summary:2-Deoxyglycosides were synthesized in high α-selectivity by the direct addition of alcohols to d-glucal and d-galactal catalyzed by TMSI and PPh3. The acid labile isopropylidene group is tolerated under this condition.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2012.06.004