Directly Regioselective Protection of Secondary Hydroxyl Group on Ribosides in Aqueous Solution

Selective benzoylation of secondary hydroxyl on sugar moiety of various ribosides including N-ribosides, O-rihosides and 2＇-deoxy-N-riboside was investigated by using benzoyl chloride and Na2CO3 in aqueous CH3CN. The influence of the aglycone and sugar moiety on the selectivity of benzoylation was d...

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Bibliographic Details
Published in:Chinese journal of chemistry 2013-06, Vol.31 (6), p.855-860
Main Authors: Xu, Ruigang, Liu, Fei, Liu, Yingju, Chen, Beiqing, Liu, Feng-Wu
Format: Article
Language:English
Subjects:
Analytical chemistry
Aqueous solutions
deoxyribosides
Peptides
protection
ribosides
secondary hydroxyl group
selective benzoylation
核苷
水溶液
碳酸钠
糖苷
羟基
苯甲酰化
苯甲酰氯
选择性保护
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Summary:Selective benzoylation of secondary hydroxyl on sugar moiety of various ribosides including N-ribosides, O-rihosides and 2＇-deoxy-N-riboside was investigated by using benzoyl chloride and Na2CO3 in aqueous CH3CN. The influence of the aglycone and sugar moiety on the selectivity of benzoylation was discussed as well. A most ef- ficient method for preparation of 2＇,3＇-O-dibenzoylnucleosides was developed.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201300045