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

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 
• 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 
• 194997-04-1 C₁₇H₁₉NO₆ 
• 194997-03-0 2-O-allyl-1,6-anhydro-4-O-benzoyl-3-oxo-β-D-arabino-hexopyranose 

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.

Intra- and intermolecular 1,3-dipolar cycloaddition of sugar ketonitrones with mono-, di-, and trisubstituted dipolarophiles

The 1,3-dipolar cycloaddition of sugar ketonitrones is a useful synthetic procedure to build up nitrogenated quaternary centers in terms of scope (substrate, dipolarophile, inter- and intramolecular versions), yield, and regio- and stereoselectivity. The

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

Carbohydrates to carbocycles: Synthesis of the densely functionalized carbocyclic core of tetrodotoxin by radical cyclization of an anhydro sugar precursor

The core of tetrodotoxin is a densely functionalized carbocycle for which an annulated pyranose can be envisaged as a retron. The carbocyclic ring is constructed upon a rigid 1,6-anhydro template which permits the early introduction of the key angular nit

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.

NOVEL REACTIONS OF CARBOHYDRATES DISCOVERED EN ROUTE TO NATURAL PRODUCTS

An approach to the synthesis of tetrodotoxin is described in which two key reactions are used to establish the densely functionalized carbocyclic ring.The -bicyclic framework of 1,6-anhydro mannopyranose serves as the the template, and in the first

Asymmetric synthesis of enantiomerically pure (-)-(1'R,4'R)-dioxolane-thymine and its anti-HIV activity

An asymmetric synthesis leading to the enantiomerically pure dioxolane-T has been achieved and its crystal structure has been determined and compared to the previously reported racemate. (-)-(1'R,4'R)-dioxolane-T was found to have potent and selective ant