Cooperative Catalysis in Glycosidation Reactions with O-Glycosyl Trichloroacetimidates as Glycosyl Donors

Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′‐Diarylthiourea as cocatalyst enforces an SN2‐type acid‐catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O‐(α‐glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β‐glycosides...

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Published inAngewandte Chemie International Edition Vol. 52; no. 38; pp. 10089 - 10092
Main Authors Geng, Yiqun, Kumar, Amit, Faidallah, Hassan M., Albar, Hassan A., Mhkalid, Ibrahim A., Schmidt, Richard R.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 16.09.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Acetamides - chemistry
acid-base catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
Chloroacetates - chemistry
cooperativity
Glycosylation
Hydrogen bonding
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
organocatalysis
Physical Sciences
Science & Technology
Stereoisomerism
thiourea
Thiourea - chemistry
Thioureas
organocatalysis
ACTIVATION
thiourea
cooperativity
RECOGNITION
acid-base catalysis
PHOSPHATES
glycosylation
RECEPTORS
BINDING
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Summary:Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′‐Diarylthiourea as cocatalyst enforces an SN2‐type acid‐catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O‐(α‐glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β‐glycosides are preferentially or exclusively obtained.
Bibliography:University of Konstanz
Deanship of Scientific Research (DSR)
ark:/67375/WNG-VFNLZ5V6-9
The authors acknowledge the generous support of this work by the University of Konstanz. This paper was also funded by the Deanship of Scientific Research (DSR), King Abdulaziz University under grant No. 26-3-1432/HiCi. The authors therefore acknowledge technical and financial support of KAU.
ArticleID:ANIE201302158
King Abdulaziz University - No. 26-3-1432/HiCi
istex:6E889E5A7C833193C037C8A59DCD62E97E7FC1F4
The authors acknowledge the generous support of this work by the University of Konstanz. This paper was also funded by the Deanship of Scientific Research (DSR), King Abdulaziz University under grant No. 26‐3‐1432/HiCi. The authors therefore acknowledge technical and financial support of KAU.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201302158