166383-69-3

Basic information

• Product Name: (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine
• Synonyms: (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine
• CAS NO: 166383-69-3
• Molecular Weight: 307.39
• Mol File: 166383-69-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine(166383-69-3)
• EPA Substance Registry System: (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine(166383-69-3)

Safety Data

• Hazardous Substances Data: 166383-69-3(Hazardous Substances Data)

Upstream product

• 174541-87-8 (2R,3R)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-5-<(β-naphthyl)sulphonyloxy>-3-pentanol 
• 166383-82-0 (2R,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153805-45-9 (4R,5R)-4-(benzyloxy)methyl-5-(2-hydroxyethyl)-2-oxo-oxazolidine 
• 153805-41-5 methyl (4R,5R)-4-(benzyloxy)methyl-2-oxo-5-oxazolidineacetate 
• 174541-85-6 (4R,5R)-4-Benzyloxymethyl-5-(2-chloro-ethyl)-oxazolidin-2-one 
• 174541-86-7 (2R,3R)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-3,5-pentandiol 

Downstream Products

• 567-35-1 (2S,3R)-3-hydroxyproline 
• 166383-70-6 (2R,3S)-1-t-Butoxycarbonyl-3-benzoyloxy-2-benzyloxymethylpyrrolidine 
• 166383-71-7 (3S)-1-t-butoxycarbonyl-3-benzoyloxy-N-t-butyl-L-prolinamide 
• 182556-78-1 (2S,3S)-3-Benzoyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 174541-88-9 (2R,3S)-1-(tert-butoxycarbonyl)-2-(benzyloxymethyl)-3-<(4-nitrobenzoyl)oxy>-pyrrolidine 
• 166383-82-0 (2R,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 174541-89-0 (2R,3S)-1-(tert-butoxycarbonyl)-2-(benzyloxymethyl)-3-hydroxypyrrolidine 
• 98900-30-2 (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidinium hydrochloride 

Relevant articles and documents

Inhibitors of HIV protease

Compounds of formula (I): STR1 wherein: R1 is hydrogen, alkyl, aralkyl, --CORa, --CORb, --CSRa, --CSRb, --SO2 Rb, --CONHRb, --CSNHRb, --CONRb Rb or --CSNRb Rb ; R2 is hydrogen or alkyl; R3 is hydrogen, alkylidene, substituted alkyl, or Rb ; R4 is optionally substituted alkyl, cycloalkyl, or aryl; R5 is Rb O--, Rb Rb N--, Rb HN--, aralkyloxycarbonyloxy or aralkyloxycarbonylamino, or R5 is --(CH2)p --D--(CH2)r --, where D is a single bond, carbonyl, oxygen, sulfur, --NH--, --(CH2 =CH2)-- or --NHCO--; and p and r are each 0 or an integer from 1 to 5; A is --(CH2)m --B--(CH2)n -- where B is a single bond, carbonyl, oxygen, sulfur, --NH--, --(CH2 =CH2)-- or --NHCO--; and m and n are each 0 or an integer from 1 to 5; Ra is alkoxy, aralkyloxy, aryloxy or alkoxycarbonyl; Rb is optionally substituted alkyl, cycloalkyl, heterocyclic, aryl or arylalkenyl; and pharmaceutically acceptable salts and esters thereof and pro-drugs therefor, have the ability to inhibit the activity of HIV protease and may thus be used for the treatment and prophylaxis of AIDS.

A straightforward synthesis of (2S,3R)-3-hydroxyproline and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine

A stereocontrolled synthesis of (2S,3R)-3-hydroxyproline 1, and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine 2 has been achieved in 21% and 38% yield via the homochiral 4,5-disubstituted oxazolidin-2-one 3. The trans relationship in 2 has been introduced by a modified Mitsunobu reaction.