200616-22-4

Basic information

• Product Name: 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-
• CAS NO: 200616-22-4
• Molecular Formula: C24H27NO2
• Molecular Weight: 361.484
• Mol File: 200616-22-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-(200616-22-4)
• EPA Substance Registry System: 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-(200616-22-4)

Safety Data

• Hazardous Substances Data: 200616-22-4(Hazardous Substances Data)

Upstream product

• 474022-71-4 (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol 
• 189562-37-6 (3S)-3-(N,N-dibenzyl)amino-1-hydroxy-1-methylthio-2-oxo-4-phenylbutane 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 127927-43-9 N,N-dibenzyl-3(S)-amino-1,2(S)-epoxy-4-phenylbutane 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 184537-69-7 (3S)-3-(N,N-dibenzyl)amino-1-methylsulfinyl-2-oxo-4-phenylbutane 

Downstream Products

• 147915-02-4 (2S,3S)-3-amino-4-phenylbutane-1,2-diol 
• 62023-65-8 (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 

Relevant articles and documents

Totally selective ring-opening of amino epoxides with ketones: A general entry to enantiopure (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols

(Chemical Equation Presented) Transformation of enantiopure diastereoisomers (2R,1′S)- and (2S,1′S)-2-(1-aminoalkyl)epoxides into the corresponding 4-(1-aminoalkyl)-1,3-dioxolanes is achieved by reaction with different ketones in the presence of BF3

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.