43138-33-6

Upstream product

• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 2816-87-7 1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose 
• 28642-57-1 1,2-O-Isopropyliden-D-glucofuranose-3-p-toluolsulfonat 
• 3253-75-6 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 2946-01-2 (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 75646-85-4 3-p-toluenesulphonate of 1,2-O-isopropylidene-5,6-O-methoxymethylidene-α-D-glucofuranose 
• 15919-16-1 5-β-formyl-4-β-O-tosyl-2α,3α-O-isopropylidenetetrahydrofuran 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 2872-64-2 1,2-O-Isopropyliden-3-O-p-toluolsulfonyl-α-D-glucofuranose-5,6-thionocarbonat 

Downstream Products

• 62102-11-8 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose 
• 78785-02-1 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose 
• 289665-51-6 6-O-benzoyl-5-deoxy-1,4:2,3-dianhydro-D-allitol 
• 289665-57-2 3'-deoxy-3'-(uracil-1-yl)-5'-deoxy-1',4'-anhydro-D-altritol 
• 289665-56-1 2'-deoxy-2'-(uracil-1-yl)-5'-deoxy-1',4'-anhydro-D-altritol 
• 289665-64-1 2'-deoxy-2'-(thymin-1-yl)-5'-deoxy-1',4'-anhydro-D-altritol 
• 289665-47-0 Benzoic acid 2-[(2R,3R,4S)-4-hydroxy-3-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-ethyl ester 
• 289665-46-9 6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose 
• 289665-53-8 6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol 

Relevant academic research and scientific papers

Synthesis of isoaristeromycin from D-glucose

Isoaristeromycin 1, an analogue of the nucleoside antibiotic aristeromycin, has been synthesized by the application of intermolecular nitrone cycloaddition (INC) reaction on a D-glucose derived substrate.

Novel isonucleoside analogues: synthesis of 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol

A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in 11 steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis of (1R, 2R, 4S, 5R)-2,4-Dihydroxy-5-hydroxymethylcyclopentylamine and its Conversion to an Analogue of Aristeromycin

Isoaristeromycin (1), an isomer of the nucleoside antibiotic aristeromycin, has been synthesized in twelve steps from D-glucose.

Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose

The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.