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Integrated route to the L ‐aldohexoses using a common man‐made chiral building block
Author(s) -
Takeuchi Miwako,
Taniguchi Takahiko,
Ogasawara Kunio
Publication year - 2000
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/(sici)1520-636x(2000)12:5/6<338::aid-chir6>3.0.co;2-y
Subject(s) - chemistry , block (permutation group theory) , mannose , organic chemistry , combinatorics , mathematics
Starting from a common man‐made chiral sugar building block, five out of eight L ‐aldohexoses have been synthesized in a diastereocontrolled manner to complete an integrated synthesis of the eight possible aldohexoses; the remaining three L ‐hexoses were synthesized from the same building block. Thus, L ‐altrose, L ‐mannose, L ‐allose, L ‐talose, and L ‐glucose were obtained in the present investigation on the basis of the inherent convex‐face selectivity exerted by the chiral building block. Chirality 12:338–341, 2000. © 2000 Wiley‐Liss, Inc.