225640-79-9

Upstream product

• 116-11-0 2-Methoxypropene 
• 130782-54-6 4-cyanophenyl 1,5-dithio-β-D-arabinopyranoside 
• 225640-84-6 4-cyanophenyl 2,3-O-isopropylidene-1,5-dithio-α-L-threo-pentopyranosid-4-ulose 

Downstream Products

• 225640-84-6 4-cyanophenyl 2,3-O-isopropylidene-1,5-dithio-α-L-threo-pentopyranosid-4-ulose 
• 232257-69-1 4-cyanophenyl 4-deoxy-4-iodo-2,3-O-isopropylidene-1,5-dithio-α-L-arabinopyranoside 
• 232257-72-6 4-cyanophenyl 1,5-dithio-β-D-glycero-pentopyranosid-3-ulose 
• 232257-71-5 4-cyanophenyl 2,3-O-isopropylidene-1,5-dithio-β-D-glycero-pent-3-enopyranoside 
• 225641-09-8 4-cyanophenyl 4-acetamido-4-deoxy-2,3-O-isopropylidene-1,5-dithio-α-L-arabinopyranoside 

Relevant academic research and scientific papers

Synthesis of the 2- and 4-monomethyl ethers and the 4-deoxy-4-fluoro derivative of 4-cyanophenyl 1,5-dithio-β-D-xylopyranoside as potential antithrombotic agents

The title glycoside undergoes acetonation with 2-methoxypropene to give a 2:1 mixture of the crystalline 2,3- and 3,4-isopropylidene acetals in 94% yield, which upon methylation under controlled conditions followed by deacetonation afforded the respective 4- and 2-monomethyl ethers. The 2,3-acetal underwent reaction with diethylaminosulfur trifluoride to introduce fluorine at C-4 with net retention of stereochemistry, but the 3,4-acetal under comparable conditions underwent migration of the arylthio group to C-2 and fluorination at C-1, with stereochemical retention at both positions. The title glycoside undergoes acetonation with 2-methoxypropene to give a 2:1 mixture of the crystalline 2,3- and 3,4-isopropylidene acetals in 94% yield, which upon methylation under controlled conditions followed by deacetonation afforded the respective 4- and 2-monomethyl ethers. The 2,3-acetal underwent reaction with diethylaminosulfur trifluoride to introduce fluorine at C-4 with net retention of stereochemistry, but the 3,4-acetal under comparable conditions underwent migration of the arylthio group to C-2 and fluorination at C-1, with stereochemical retention at both positions.

Chemical interconversions of 4-cyanophenyl 1,5-dithio-β-D-xylopyranoside (Beciparcil): Structural modification at the C-4 position

The title dithioxyloside 1, an orally active antithrombotic agent, as its 2,3-isopropylidene acetal, was converted into the corresponding glycos-4-ulose, which served as precursor via reduction to the 4-epimer of 1 and via oximation-reduction to the 4-acetamido-4-deoxy 4-epimer of 1. Copyright (C) 1998 Elsevier Science Ltd.