191083-76-8

Basic information

• Product Name: Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester
• Synonyms: Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester
• CAS NO: 191083-76-8
• Molecular Weight: 477.475
• Mol File: 191083-76-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester(191083-76-8)
• EPA Substance Registry System: Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester(191083-76-8)

Safety Data

• Hazardous Substances Data: 191083-76-8(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 191083-75-7 ((2S,3S,4S,5S)-3-Azido-5-ethoxy-4-hydroxy-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester 
• 191083-74-6 ((3aS,4S,6S,6aS)-6-Ethoxy-2,2-dioxo-tetrahydro-2λ⁶-furo[3,4-d][1,3,2]dioxathiol-4-ylmethyl)-phosphonic acid diethyl ester 
• 191083-69-9 ((2S,3R,4S,5S)-5-Ethoxy-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester 
• 191083-70-2 ethyl 2,3-O-isopropylidene-α-D-lyxo-furanoside 
• 191083-71-3 ethyl 5-deoxy-5-iodo-2,3-O-isopropylidene-α-D-lyxofuranoside 
• 1114-34-7 D-lyxose 
• 63087-96-7 methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-α-D-lyxofuranoside 
• 63029-07-2 methyl 2,3-O-isopropylidene-α-D-lyxofuranoside 
• 191083-72-4 ((3aR,4S,6S,6aS)-6-Ethoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-phosphonic acid diethyl ester 
• 191083-67-7 ((3aR,4S,6S,6aS)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-phosphonic acid diethyl ester 
• 191083-73-5 ((3aS,4S,6S,6aS)-6-Ethoxy-2-oxo-tetrahydro-2λ⁴-furo[3,4-d][1,3,2]dioxathiol-4-ylmethyl)-phosphonic acid diethyl ester 

Relevant articles and documents

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.