A facile synthesis of 4,6- O-benzylidene- d-glycals via 1,5-anhydro-4,6- O-benzylidene- d-hex-1-en-3-ulose

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.

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Veröffentlicht in:Carbohydrate research 2008-11, Vol.343 (16), p.2740-2743
Hauptverfasser: Sakakibara, Tohru, Ito, Tsubasa, Kotaka, Chika, Kajihara, Yasuhiro, Watanabe, Yuhya, Fujioka, Aki
Format: Artikel
Sprache:eng
Schlagworte:
1-En-3-ulose
Benzylidenation
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Carbohydrate Conformation
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Carbohydrates - isolation & purification
Glycal
Lipase PS
Quantum Theory
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Zusammenfassung: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.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2008.05.018