Synthesis of 2,3:4,6-di- O-isopropylidene- d-allopyranose from d-glucose

[Display omitted] 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/CaCO 3.

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Bibliographic Details
Published in:Carbohydrate research 2005-08, Vol.340 (11), p.1872-1875
Main Authors: Gómez, Ana M., Company, María D., Agocs, Attila, Uriel, Clara, Valverde, Serafín, López, J. Cristóbal
Format: Article
Language:English
Subjects:
2,3:4,6-Di- O-isopropylidene- d-allopyranose
Carbohydrate acetals
Carbohydrate Conformation
Carbohydrates - chemistry
Disaccharides - chemistry
Glucose - chemistry
Glycosides - chemistry
Heterocyclic Compounds, 3-Ring - chemical synthesis
Hexoses - chemical synthesis
Magnetic Resonance Spectroscopy
Models, Chemical
NBS
Oligosaccharides - chemistry
Phenyl 1-thio-glycosides
Temperature
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Description
Summary:[Display omitted] 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/CaCO 3.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2005.05.011