Dual Stereoselectivity of 1‐(2′‐Carboxy)benzyl 2‐Deoxyglycosides as Glycosyl Donors in the Direct Construction of 2‐Deoxyglycosyl Linkages | Zendy

Kim Kwan Soo | Zendy; Park Jin | Zendy; Lee Yong Joo | Zendy; Seo Yong Sung | Zendy

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Dual Stereoselectivity of 1‐(2′‐Carboxy)benzyl 2‐Deoxyglycosides as Glycosyl Donors in the Direct Construction of 2‐Deoxyglycosyl Linkages

Author(s) -

Kim Kwan Soo,

Park Jin,

Lee Yong Joo,

Seo Yong Sung

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200390139

Subject(s) - stereoselectivity , glycosyl , glycosylation , chemistry , glycosyl donor , stereochemistry , organic chemistry , catalysis , biochemistry

Different protecting groups on the glycosyl donor changes the stereoselectivity of the new glycosylation reaction shown in the scheme. Glycosylation of CB 4,6‐ O ‐benzylidene‐2‐deoxyglycoside 1 with secondary alcohol acceptors gave predominantly β‐disaccharides 3 , whereas the same reaction with CB tri‐ O ‐benzyl‐2‐deoxyglycoside 2 afforded α‐disaccharides 4 . CB=(2′‐carboxy)benzyl.

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