A facile synthesis of 4,6-O-benzylidene-D-glycals via 1,5-anhydro-4,6-O-benzylidene-D-hex-1-en-3-ulose.
Benzylidenation of readily available 1,5-anhydro-D-hex-1-en-3-ulose, followed by sodium borohydride reduction, afforded the title compounds in high yields. Separation of 4,6-O-benzylidene-D-allal and -D-glucal was accomplished by selective acetylation with lipase PS.
Sakakibara
Tohru
T
Department of Chemistry, Graduate School of Integurated Science, Yokohama City University, Seto Kanazawa-ku, Yokohama 236, Japan. baratoru@yokohama-cu.ac.jp
Ito
Tsubasa
T
Kotaka
Chika
C
Kajihara
Yasuhiro
Y
Watanabe
Yuhya
Y
Fujioka
Aki
A
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D011789:Quantum Theory
D019086:Bridged Bicyclo Compounds, Heterocyclic; D002241:Carbohydrates