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Stereoselective Synthesis of 3-C-Branched-Chain Sugars by Aldol Reaction of Furanos-3-Uloses with Acetone
Titel:
Stereoselective Synthesis of 3-C-Branched-Chain Sugars by Aldol Reaction of Furanos-3-Uloses with Acetone
Auteur:
Calvo-mateo, Ana Camarasa, Maria-Jose Diaz-Ortiz, Angel Heras, Federico G. De las Alemany, Antonio
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 8 (1989) nr. 3 pagina's 395-404
Jaar:
1989-07-01
Inhoud:
Aldol reaction of 1,2-O-isopropylidene-5-O-tertbutyl-dimethylsilyl-α-D-erythro-pentofuranos-3-ulose (1) with acetone in the presence of aqueous K2CO3 afforded 3-C-acetonyl-1,2-O-isopropylidene-5-O-tertbutyl-dimethylsilyl-α-D-ribofuranose(2). Similar reaction of 1,2:5, 6-di-o-isopropylidene- α-D-ribo-hexofuranos-3-ulose (3) afforded 3-C-acetonyl-1,2:5, 6-di-o-isopropylidene- α-D-allofuranose (4) and (1R, 3R, 7R, 8S, 10R)-perhydro-8-hydroxy-5,5,10-trimethyl-2,4,6,11,14-pentaoxatetracyclo[8,3,1,01,8,03,7] tetradecane. The stereochemistry of the new chiral centers were determined by 1H NOE experiments.
Uitgever:
Taylor & Francis
Bronbestand:
Elektronische Wetenschappelijke Tijdschriften
Details van artikel 142 van 252 gevonden artikelen