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Directly Regioselective Protection of Secondary Hydroxyl Group on Ribosides in Aqueous Solution
Author(s) -
Xu Ruigang,
Liu Fei,
Liu Yingju,
Chen Beiqing,
Liu FengWu
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300045
Subject(s) - chemistry , moiety , aqueous solution , regioselectivity , aglycone , chloride , organic chemistry , selectivity , riboside , combinatorial chemistry , medicinal chemistry , catalysis , glycoside , biochemistry
Selective benzoylation of secondary hydroxyl on sugar moiety of various ribosides including N ‐ribosides, O ‐ribosides and 2′‐deoxy‐ N ‐riboside was investigated by using benzoyl chloride and Na 2 CO 3 in aqueous CH 3 CN. The influence of the aglycone and sugar moiety on the selectivity of benzoylation was discussed as well. A most efficient method for preparation of 2′,3′‐ O ‐dibenzoylnucleosides was developed.