873550-81-3

Basic information

• Product Name: dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate
• Synonyms: dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate
• CAS NO: 873550-81-3
• Molecular Weight: 447.428
• Mol File: 873550-81-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate(873550-81-3)
• EPA Substance Registry System: dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate(873550-81-3)

Safety Data

• Hazardous Substances Data: 873550-81-3(Hazardous Substances Data)

Upstream product

• 84252-35-7 ((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 70831-49-1 (4S,5S)-4-hydroxymethyl-2,2-dimethyl-5-tosyloxymethyl-1,3-dioxolane 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 873550-72-2 (2S,3S)-4-azido-2,3-O-isopropylidene-2,3-dihydroxybutanal 
• 17176-77-1 Dibenzyl phosphite 

Downstream Products

• 875113-02-3 dibenzyl (1R,2R,3S)-1,2,3-trihydroxy-2,3-O-isopropylidene-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate 
• 875113-08-9 dibenzyl (1R,2R,3S)-2,3-dihydroxy-2,3-O-isopropylidene-1-methoxy-4-[(4-methoxycarbonyl)-1,2,3-triazol-1-yl]butylphosphonate 

Relevant articles and documents

Enantiomerically pure 4-amino-1,2,3-trihydroxybutylphosphonic acids

(1S,2R,3S)-, (1R,2R,3S)- and (1S,2R,3R)-4-amino-1,2,3- trihydroxybutylphosphonic acids were synthesised. The synthetic strategy involved preparation of the respective 4-azido-2,3-O-isopropylidene-l-threose or -d-erythrose, addition of dialkyl phosphites, separation of C-1 epimeric O,O-dibenzyl phosphonates, the reduction of azides and the removal of the protecting groups. The (2R,3S) and (2R,3R) configurations in the final products were secured by employing diethyl l-tartrate and d-isoascorbic acid as starting materials. The stereochemical course of the addition to the carbonyl groups in 4-azido-2,3-O-isopropylidene-l-threose or -d-erythrose followed that established earlier for 2,3-O-isopropylidene-d-glyceraldehyde and similar (3:1-4:1) diastereoselectivities were achieved.