473916-49-3

Basic information

• Product Name: (2R,3S)-1,2-O-isopropylidene-3-(t-butoxycarbonyl)amino-4-phenybutane-1,2-diol
• Synonyms: (2R,3S)-1,2-O-isopropylidene-3-(t-butoxycarbonyl)amino-4-phenybutane-1,2-diol
• CAS NO: 473916-49-3
• Molecular Weight: 321.417
• Mol File: 473916-49-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-1,2-O-isopropylidene-3-(t-butoxycarbonyl)amino-4-phenybutane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-1,2-O-isopropylidene-3-(t-butoxycarbonyl)amino-4-phenybutane-1,2-diol(473916-49-3)
• EPA Substance Registry System: (2R,3S)-1,2-O-isopropylidene-3-(t-butoxycarbonyl)amino-4-phenybutane-1,2-diol(473916-49-3)

Safety Data

• Hazardous Substances Data: 473916-49-3(Hazardous Substances Data)

Upstream product

• 166249-17-8 methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 92973-40-5 methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 92973-39-2 O³,O⁴-(1-methylethylidene)-L-threonic acid 
• 473916-42-6 (S)-tert-butyl 2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)aziridine-1-carboxylate 
• 100-59-4 phenylmagnesium chloride 
• 473916-39-1 (2R,3S)-1-azido-2-hydroxy-3,4-isopropylidenebutane-2,3,4-triol 

Downstream Products

• 170359-21-4 C₂₂H₂₉NO₆S 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 99113-35-6 ((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester 

Relevant articles and documents

From L-ascorbic acid to protease inhibitors: Practical synthesis of key chiral epoxide intermediates for aspartyl proteases

Efficient synthetic routes were developed to prepare a sizable amount (4-15 grams) of the chiral epoxides 4-6 as versatile intermediates for the synthesis of aspartyl protease inhibitors of therapeutic interest such as HIV protease and β-secretase. Oxidative cleavage of the C(2)-C(3) double bond of L-ascorbic acid followed by functional group manipulation led to the preparation of the epoxide 10, which was opened with an azide to yield a common aziridine intermediate 12. Through opening of the aziridine ring of 12 with either a carbon or a sulfur nucleophile, chiral epoxide precursors 4-6 could be prepared for various HIV protease inhibitors. Except for the final low melting epoxides 5 and 6, all intermediates were obtained as crystalline solids, thus the synthetic pathway can be easily applied to a large-scale synthesis of the chiral epoxides.