147915-02-4

Basic information

• Product Name: 1,2-Butanediol, 3-amino-4-phenyl-, (2S,3S)-
• CAS NO: 147915-02-4
• Molecular Formula: C10H15NO2
• Molecular Weight: 181.235
• Mol File: 147915-02-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,2-Butanediol, 3-amino-4-phenyl-, (2S,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Butanediol, 3-amino-4-phenyl-, (2S,3S)-(147915-02-4)
• EPA Substance Registry System: 1,2-Butanediol, 3-amino-4-phenyl-, (2S,3S)-(147915-02-4)

Safety Data

• Hazardous Substances Data: 147915-02-4(Hazardous Substances Data)

Upstream product

• 147915-01-3 (2S,3S)-3-azido-1,2-O-methylethylidene-4-phenylbutane-1,2-diol 
• 140867-27-2 (2R,3R)-1,2-O-methylethylidene-4-phenylbutane-1,2,3-triol 
• 591-51-5 phenyllithium 
• 78571-81-0 (R,R)-3-(phenylmethyl)oxiranemethanol 
• 474022-71-4 (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 200616-22-4 (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol 
• 116949-67-8 (2S,3S)-2-azido-1-phenyl-butane-3,4-diol 

Downstream Products

• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 162221-36-5 (4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid methyl ether 
• 147976-18-9 (4S,5S)-4-benzyl-2-oxo-oxazolidine-5-carboxylic acid 
• 207281-54-7 Methanesulfonic acid (1S,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propyl ester 
• 207281-52-5 2-[(1S,2S)-1-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-isoindole-1,3-dione 
• 136465-80-0 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane 
• 164394-36-9 (2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol 
• 147976-16-7 (4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone 
• 260562-78-5 ((1S,2R)-1-Benzyl-3-cyano-2-methoxymethoxy-propyl)-methyl-carbamic acid benzyl ester 
• 260562-77-4 ((1S,2R)-1-Benzyl-3-cyano-2-hydroxy-propyl)-methyl-carbamic acid benzyl ester 
• 260562-76-3 Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl ester 
• 174623-90-6 (3R,4R)-4-[(benzyloxycarbonyl)(methyl) amino]-3-(methoxymethoxy)-5-phenylpentanoic Acid 
• 128018-44-0 N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane 
• 62023-65-8 (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 

Relevant articles and documents

A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an α-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (±)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (±)-8b in 46% yield for another round of the enzymatic processing.

A General, Catalytic, and Enantioselective Synthesis of (S)-γ-[(S)-1-Aminoalkyl]-γ-lactones

A catalytic asymmetric synthesis of N-phthaloyl (S)-γ-[(S)-1-aminoalkyl]-γ-lactones, widely used intermediates in the preparation of hydroxyethylene dipeptide isosteres, is described. The highly enantiopure epoxy alcohols arising from the Sharpless epoxid