131940-20-0

Basic information

• Product Name: (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose
• Synonyms: (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose
• CAS NO: 131940-20-0
• Molecular Weight: 306.315
• Mol File: 131940-20-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose(131940-20-0)
• EPA Substance Registry System: (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose(131940-20-0)

Safety Data

• Hazardous Substances Data: 131940-20-0(Hazardous Substances Data)

Upstream product

• 4744-10-9 dimethoxypropane 
• 14440-51-8 1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose 
• 98-88-4 benzoyl chloride 
• 14168-65-1 mannosan 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 7225-53-8 (-)-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose 
• 149883-63-6 (1R,2S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-eth-(E)-ylidene]-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol 
• 149883-62-5 (1R,2S,4S,5R)-3-[2-Hydroxy-eth-(E)-ylidene]-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol 
• 149793-72-6 1,6-anhydro-4-O-benzoyl-2-O-(p-methoxybenzyl)-β-D-mannopyranose 
• 144152-57-8 2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 
• 144152-56-7 2'-methyl-(1,6-anhydro-3-deoxy-3-C-formyl-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 
• 144152-54-5 (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-4-ene 
• 144152-51-2 1,6-anhydro-4-O-benzoyl-2-O-(p-methoxybenzyl)-β-D-arabino-hexopyran-3-ulose 
• 144152-55-6 2'-methyl-(1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-3-C-vinyl-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline 
• 136884-12-3 (-)-(2R,4R,1'S)-4-(2-O-benzoyl-1-hydroxyethyl)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>dioxolane 
• 136884-11-2 (-)-(2R,4R,1'S)-4-(2-O-benzoyl-1-hydroxyethyl)-2-(hydroxymethyl)dioxolane 
• 552849-00-0 2-O-allyl-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose 

Relevant articles and documents

Synthesis of unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose via stereoselective photobromination of 2,3-isopropylidene-4-benzoyl-1,6-anhydro-β-D-mannopyranose

Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at exo-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose 6 produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose 7. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound 7.

Process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides

An asymmetric process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides. The enantiomerically pure dioxolane nucleosides are active HIV agents, that are significantly more effective than the prior prepared racemic mixtures of the

Asymmetric Synthesis of 1,3-Dioxolane-Pyrimidine Nucleosides and Their Anti-HIV Activity

In order to study the structure-activity relationships of dioxolane nucleosides as potential anti-HIV agents, various enantiomerically pure dioxolane-pyrimidine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear cells.The enantiomerically pure key intermediate 8 has been synthesized in nine steps from 1,6-anhydro-D-mannose (1), which was condensed with 5-substituted pyrimidines to obtain various dioxolane-pyrimidine nucleosides.Upon evaluation of these compounds, cytosine derivative 19 was found to exhibit the most potent anti-HIV agent although it is the most toxic.The order of anti-HIV potency was as follows: cytosine (β-isomer) > thymine > cytosine (α-isomer) > 5-chlorouracil > 5-bromouracil > 5-fluorouracil derivatives.Uracil, 5-methylcytosine, and 5-iodouracil derivatives were found to be inactive.Interestingly, α-isomer 20 showed good anti-HIV activity without cytotoxicity.As expected, other α-isomers did not exhibit any significant antiviral activity. (-)-Dioxolane-T was 5-fold less effective against AZT-resistant virus than AZT-sensitive virus.