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Synthesis of a New C(1→2)‐Linked Iminodisaccharide Starting from Levoglucosenone
Author(s) -
Navarro Isabel,
Vogel Pierre
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200201)85:1<152::aid-hlca152>3.0.co;2-l
Subject(s) - chemistry , stereochemistry , combinatorial chemistry , organic chemistry
Methyl 2‐deoxy‐2‐[(1 S )‐2,5‐dideoxy‐2,5‐imino‐ L ‐ribitol‐1‐ C ‐yl)‐ α ‐ D ‐glucopyranoside ((+)‐ 6 ) was obtained from the product of Nozaki‐Kishi coupling of 2,5‐{[( tert ‐butoxy)carbonyl]imino}‐2,5‐dideoxy‐3,4‐ O ‐isopropylidene‐ L ‐ribose ((−)‐ 9 ) and 4‐ O ‐benzyl‐6‐ O ‐[(benzyloxy)methyl]‐3‐deoxy‐2‐ O ‐[(trifluoromethyl)sulfonyl]‐ α ‐ D ‐ erythro ‐hex‐2‐enopyranoside ((+)‐ 12 ). The alkenyl triflate (+)‐ 12 was derived from levoglucosenone ( 1 ).