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TMDS as a Dual‐Purpose Reductant in the Regioselective Ring Cleavage of Hexopyranosyl Acetals to Ethers
Author(s) -
Zhang YinJie,
Dayoub Wissam,
Chen GuoRong,
Lemaire Marc
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101682
Subject(s) - regioselectivity , chemistry , cleavage (geology) , ring (chemistry) , dual role , organic chemistry , bond cleavage , stereochemistry , combinatorial chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
1,1,3,3‐Tetramethyldisiloxane (TMDS) has been developed as an excellent dual‐purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4,6‐ O ‐acetals with Cu(OTf) 2 or AlCl 3 to afford the corresponding primary and secondary ethers. Its application to the concise synthesis of carbohydrate‐based surfactants is highlighted.