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Stereoselective Synthesis of Highly Functionalized C‐ Glycosides based on Acetal [1,2] and [1,4] Wittig Rearrangements
Author(s) -
Tomooka Katsuhiko,
Yamamoto Hiroshi,
Nakai Takeshi
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001215)39:24<4500::aid-anie4500>3.0.co;2-w
Subject(s) - wittig reaction , acetal , glycoside , stereoselectivity , chemistry , stereochemistry , organic chemistry , catalysis
Two types of highly functionalized C‐glycosides were stereoselectively synthesized from an ethynylvinylmethanol‐derived O‐glycoside in one step through acetal Wittig rearrangements (see scheme). The [1,2] Wittig rearrangement affords the 1 β ‐C‐glycoside that has contiguous quarternary chiral centers at the C1 and C1′ positions, while the [1,4] Wittig rearrangement has been used for the first time in the synthesis of C‐glycosides.