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Synthese von disubstituierten Cyclopropa[ c ]pyranosiden aus 2,3‐Epoxy‐4‐triflat‐pyranosiden
Author(s) -
Zaman Fakhar,
Fatima Ayjaz,
Voelter Wolfgang
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101191
Subject(s) - chemistry , epoxy , medicinal chemistry , organic chemistry
Synthesis of Disubstituted Cyclopropa[ c ]pyranosides from 2,3‐Epoxy‐4‐triflate‐pyranosides Reaction of benzyl 2,3‐anhydro‐4‐ O ‐trifluoromethylsulfonyl‐β‐ L ‐ribopyranoside ( 1 ) and benzyl 2,3‐anhydro‐4‐ O ‐trifluoromethylsulfonyl‐α‐ D ‐ribopyranoside ( 4 ) with malonic acid derivatives yields, via the carbanions, the cyclopropa‐monosaccharides 3 and 6 . The ester residues attached to the cyclopropane moiety can be saponified to give the corresponding acids which can be coupled to new carbohydrate amino acid derivatives of type 9 which are of biological interest in different immunological assays.