923601-69-8

Basic information

• Product Name: (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester
• Synonyms: (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester
• CAS NO: 923601-69-8
• Molecular Weight: 299.798
• Mol File: 923601-69-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester(923601-69-8)
• EPA Substance Registry System: (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester(923601-69-8)

Safety Data

• Hazardous Substances Data: 923601-69-8(Hazardous Substances Data)

Upstream product

• 150935-37-8 (R)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid t-butyl ester 
• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 21685-51-8 D-phenylalanine methyl ester 
• 673-06-3 D-(R)-phenylalanine 
• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 

Downstream Products

• 156474-21-4 tert-butyl [(2R,3R)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate 
• 1402142-63-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate 

Relevant articles and documents

Biocatalytic synthesis of chiral intermediates for antiviral and antihypertensive drugs

The chiral intermediate (1S,2R) [3-chloro-2-hydroxy-1-(phenylmethyl)propyl] carbamic acid, 1,1-dimethyl-ethyl ester 2a was prepared for the total synthesis of a human immunodeficiency virus protease inhibitor, BMS-186318. The stereoselective reduction of (1S) [3-chloro-2-oxo-1(phenylmethyl)propyl] carbamic acid, 1,1-dimethylethyl ester 1 was carried out using microbial cultures, among which Streptomyces nodosus SC 13149 efficiently reduced 1 to 2a. A reaction yield of 80%, enantiomeric excess (e.e.) of 99.8%, and diastereomeric purity of 99% were obtained for chiral alcohol 2a. Chiral L-6-hydroxy norleucine 3, an intermediate in the synthesis of antihypertensive drug, was prepared by reductive amination of 2-keto-6-hydroxyhexanoic acid 4 using beef liver glutamate dehydrogenase. The cofactor NADH required for this reaction was regenerated using glucose dehydrogenase from Bacillus sp. A reaction yield of 80% and e.e. of 99.5% were obtained for L-6-hydroxynorleucine 3. To avoid the lengthy chemical synthesis of the ketoacid, a second route was developed in which racemic 6-hydroxynorleucine [readily available from hydrolysis of 5-(4-hydroxybutyl) hydantoin 5] was treated with D-amino acid oxidase from Trigonopsis variabilis to selectively convert the D-isomer of racemic 6-hydroxynorleucine to 2-keto-6-hydroxyhexanoic acid 4 and L-6-hydroxynorleucine 3. Subsequently, the 2-keto-6-hydroxyhexanoic acid 4 was converted to L-6-hydroxynorleucine by reductive amination using glutamate dehydrogenase. A reaction yield of 98% and an e.e. of 99.5% were obtained.

BISFURANYL PROTEASE INHIBITORS

The present invention provides compounds of Formula (I): wherein A, X, Q, R2-R6, m, and W have the values described herein, as well as compositions comprising such compounds. The compounds are protease inhibitors and are useful for i