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

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 
• 184537-69-7 (3S)-3-(N,N-dibenzyl)amino-1-methylsulfinyl-2-oxo-4-phenylbutane 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 127927-43-9 N,N-dibenzyl-3(S)-amino-1,2(S)-epoxy-4-phenylbutane 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 

Downstream Products

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

An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane

A precise and versatile method was developed for the synthesis of threo amino epoxide derivatives, which are useful intermediates for protease inhibitors. It involves the diastereoselective reduction of the carbonyl group of γ-N,N-dibenzyl amino α-hydroxy β-keto sulfide prepared from an amino acid, and its subsequent stereospecific conversion to an amino epoxide via acetoxy halogenation in high yield.

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.