50600-50-5

Upstream product

• 67-56-1 methanol 
• 103665-71-0 O⁵-(toluene-4-sulfonyl)-D-arabinose diethyl dithioacetal 
• 79083-42-4 methyl D-arabinofuranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 532-20-7 D-arabinofuranose 

Downstream Products

• 50600-42-5 methyl 5'-O-p-toluenesulfonyl-2,3-di-O-acetyl-D-arabinofuranoside 

Relevant academic research and scientific papers

Phosphorylated Glycoconjugates Based on Isosteviol, d-Arabinofuranose, and d-Ribofuranose

First phosphorylated glycoconjugates were synthesized in three stages on the basis of isosteviol, d-arabinofuranose, and d-ribofuranose. In the first stage, isosteviol reacted with methyl 5-O-(p-tosyl)-2,3-di-O-benzoyl-d-ribofuranoside and methyl 5-O-(p-tosyl)-2,3-di-O-benzoyl-d-arabinofuranoside to give glycoconjugates in which the diterpenoid fragment is linked through ester bond to the carbohydrate C5 atom. In the second stage, the anomeric methoxy group in the furanoside fragment was replaced by bromine, and the resulting 2,3-di-O-benzoyl-d-ribofuranosyl and 2,3-di-O-benzoyl-d-arabinofuranosyl bromides were treated with dibutyl phosphate to afford the target phosphorylated derivatives.

Novel synthesis of 5-thio-hexopyranoside: Preparation of 5-thio-D- and L-glucose and 1,6-anhydro-5-thio-L- and D-altrose

Asymmetric synthesis of both D- and L-isomers of 5-thioglucose and 1,6-anhydro-5-thioaltrose are described. The key intermediates, L- and D-threose diethylacetal derivatives, were derived by chemical transformation from D-xylose or D-arabinose and by Sharpless asymmetric dihydroxylation from γ-hydroxycrotylaldehyde diethylacetal. They transformed to γ-thiiranyl diethylacetal via trans-2,3-epoxy alcohol in seven steps. Acetic acid-promoted cyclization of γ-thiiranyl diethylacetal gave 5-thiopyranoside. Removal of the protected groups under the acidic conditions afforded 5-thio-D- and L-glucose and 1,6-anhydro-5-thio-L- and D-altrose, respectively.

New syntheses of methyl 5-thio-β-D-arabinopyranoside and (+)-biotin

Previously one of us reported that methyl 3, 4-O-isopropylidene-2-O-methanesulfonyl-5-thio-B-D-ribopyrano side (1) readily underwent ring contraction in methanol to give 2,5-dideoxy-2, 5-epithio-D-arabinose dimethyl acetal (2). It was of interest to exami