Synthesis of 2,3:4,6-di-O-isopropylidene-D-allopyranose from D-glucose.
2,3:4,6-Di-O-isopropylidene-d-allopyranose can be conveniently prepared from d-glucose via a synthetic sequence, which includes Mitsunobu inversion at O-3, di-O-isopropylidenation of phenyl-1-thio-d-alloside and anomeric deprotection on treatment with NBS/CaCO3.
Gómez
Ana M
AM
Instituto de Química Orgánica General (CSIC), Juan de la Cierva 3, E-28006 Madrid, Spain. anago@iqog.csic.es
Company
María D
MD
Agocs
Attila
A
Uriel
Clara
C
Valverde
Serafín
S
López
J Cristóbal
JC
D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D006601:Hexoses / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009844:Oligosaccharides / Q000737:chemistry; D013696:Temperature
C505968:2,3-4,6-di-O-isoopropylideneallopyranose; D002241:Carbohydrates; D004187:Disaccharides; D006027:Glycosides; D006575:Heterocyclic Compounds, 3-Ring; D006601:Hexoses; D009844:Oligosaccharides; D005947:Glucose