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The Selective Blocking of trans ‐Diequatorial, Vicinal Diols; Applications in the Synthesis of Chiral Building Blocks and Complex Sugars
Author(s) -
Ziegler Thomas
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199422721
Subject(s) - vicinal , acetal , blocking (statistics) , diol , cyclohexane , chemistry , monosaccharide , stereochemistry , organic chemistry , computer science , computer network
Use of the dispiroketal (Dispoke) and cyclohexane‐1,2‐diacetal (CDA) protecting groups enables the highly selective blocking of vicinal, trans ‐diequatorial diols in the presence of cis ‐ 1,2 ‐ and cis ‐ 1,3 ‐diols. In particular for monosaccharides in which the selective blocking of individual hydroxyl functions is often difficult, Dispoke and CDA groups can be a useful extension of classical acetal protecting groups like benzylidene for 1,3‐diols and isopropylidene for cis ‐1,2‐diols.