7225-53-8

Upstream product

• 131940-20-0 (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose 
• 98-88-4 benzoyl chloride 
• 14168-65-1 mannosan 
• 14440-51-8 1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose 

Downstream Products

• 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 
• 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 
• 194997-04-1 C₁₇H₁₉NO₆ 
• 194997-03-0 2-O-allyl-1,6-anhydro-4-O-benzoyl-3-oxo-β-D-arabino-hexopyranose 
• 552849-00-0 2-O-allyl-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 

Relevant academic research and scientific papers

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

Enantiomerically pure β-D-dioxolane-nucleosides

A method and composition for the treatment of humans infected with HIV that includes the administration of an HIV treatment amount of an enantiomerically pure β-D-dioxolanyl purine nucleoside of the formula: STR1 wherein R is OH, Cl, NH2, or H,

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

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

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 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.

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