191083-70-2

Upstream product

• 64-17-5 ethanol 
• 1114-34-7 D-lyxose 
• 67-64-1 acetone 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 228862-98-4 ethyl 2,3-O-isopropylidene-α-D-mannofuranoside 
• 59122-84-8 ethyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside 
• 228862-99-5 ethyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 

Downstream Products

• 191083-76-8 Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Synthesis of C-(D-glycopyranosyl)ethylamines and C-(D-glycofuranosyl)methylamines as potential glycosidase inhibitors

The C-glucosyl aldehyde, 2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal was prepared from the C-glucopyranosyl propene precursor by ozonolysis. Reductive amination of the C-glucosyl aldehyde and subsequent deprotection gave 1-anilino-2-C-(α-D-glucopyranosyl)ethane. The E and Z isomers of the oxime derivative, 1-C-(α-D-arabinofuranosyl)methanal oxime were prepared by treating their aldehyde precursor with hydroxylamine. Acetylation of the oxime, followed by catalytic hydrogenation and deprotection, gave the corresponding 1-C-(α-D-arabinofuranosyl)methylamine. Reductive amination of ethyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside using aniline gave ethyl 5-anilino-5-deoxy-D-lyxo-furanoside. Inhibition studies with these compounds on β-D-glucosidase from sweet almond, using o-nitrophenyl D-glucopyranoside as substrate, were carried out. Copyright (C) 1999 Elsevier Science Ltd.

2,3-Aziridino-2,3-dideoxy-D-ribono-γ-lactone 5-Phosphonate: Stereocontrolled Synthesis from D-Lyxose and Unusual Aziridine Ring Opening

The synthesis of (1R,4S,5S)-N-(benzyloxycarbonyl)-4-[(diethoxyphosphinyl)methyl]-3-oxa-6- azabicyclo[3.1.0]hexan-2-one (23), a new member of the 2,3-aziridino γ-lactone family of compounds, was achieved in 15 steps from D-lyxose. Like all aziridino γ-lactones known so far, 23 reacted with a soft nucleophile (ethanethiol) to give exclusively the product of aziridine ring opening at C-2 (24). On the other hand, hard nucleophiles (alcohols) did not react directly with the aziridine ring of 23 but appeared to promote intramolecular attack of the aziridine ring at C-3 by the C-5 phosphonate group, resulting, after hydrolytic workup, in formation of the 2-amino-3-hydroxy-D-ribono-1,4-lactone derivatives 25 and 26, instead of the expected 2-amino-3-alkoxy-D-xylono-1,4-lactone derivatives.