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New optically active 1,3‐oxathiolanes
Author(s) -
Kraus JeanLouis,
Attardo Giorgio
Publication year - 1993
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530050210
Subject(s) - chemistry , alkoxy group , enantiomer , salt (chemistry) , optically active , nucleoside , stereochemistry , medicinal chemistry , organic chemistry , alkyl
cis ‐ and trans ‐5‐Ethoxy‐1,3‐oxathiolane‐2‐carboxylic acids were obtained in pure form. The cis isomer was resolved into its enantiomers through diastereoisomeric salt formation with enantiomerically pure α‐methylbenzylamine. Reduction of the salt followed by benzoylation led to 2‐benzoyloxymethyl‐5‐ethoxy‐2(R)‐5(S)‐1,3‐oxathiolane and 2‐benzoyloxymethyl‐5‐ethoxy‐2(S)‐5(R)‐1,3‐oxathiolane, useful intermediates in nucleoside chemistry. © 1993 Wiley‐Liss, Inc.