176972-62-6

Basic information

• Product Name: METHYL (1S,2S)-1-BENZYL-3-CHLORO-2-HYDROXYPROPYLCARBAMATE
• Synonyms: METHYL (1S,2S)-1-BENZYL-3-CHLORO-2-HYDROXYPROPYLCARBAMATE
• CAS NO: 176972-62-6
• Molecular Formula: C₁₂H₁₆ClNO₃
• Molecular Weight: 0
• Mol File: 176972-62-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL (1S,2S)-1-BENZYL-3-CHLORO-2-HYDROXYPROPYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (1S,2S)-1-BENZYL-3-CHLORO-2-HYDROXYPROPYLCARBAMATE(176972-62-6)
• EPA Substance Registry System: METHYL (1S,2S)-1-BENZYL-3-CHLORO-2-HYDROXYPROPYLCARBAMATE(176972-62-6)

Safety Data

• Hazardous Substances Data: 176972-62-6(Hazardous Substances Data)

Upstream product

• 176972-61-5 (S)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid methyl ester 
• 63-91-2 L-phenylalanine 
• 100-99-2 triisobutylaluminum 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 136522-18-4 2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 137431-06-2 2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 127779-20-8 Saquinavir 

Relevant articles and documents

Chiral chlorohydrins from the biocatalyzed reduction of chloroketones: Chiral building blocks for antiretroviral drugs

E. coli cells that contain overexpressed alcohol dehydrogenases (ADHs) were screened as biocatalysts for the stereoselective reduction of chloroketones 5 a-d, the corresponding halohydrins 6 a-d of which are building blocks in the synthesis of antiretroviral drugs. Among them, ADH from Sphingobium yanoikuyae was found to reduce chloroketone 5 c with a high stereoselectivity (90 % de) and conversion (85 %) to furnish threo halohydrin (R,S)-6 c. ADH from Ralstonia sp. (RasADH) was able to reduce 5 a and 5 b with complementary diastereoselectivity to provide access to both threo and erythro halohydrins through "substrate-based" stereocontrol. The RasADH-catalyzed reductions were optimized to provide (R,S)-6 a with 98 % conversion and 84 % diastereomeric excess (de) and (S,S)-6 b with 95 % conversion and 86 % de. Molecular modeling studies showed that 5 b, which features a carboxybenzyl protecting group, is able to bind to the enzyme catalytic site in an "inverted" mode in comparison to tert-butyloxycarbonyl- and methyloxycarbonyl-protected substrates 5 a and 5 c, which sheds light on the observed switching of the stereopreference. RasADH-catalyzed reductions were optimized to provide (R,S)-6 a with 98 % conversion and 84 % de and (S,S)-6 b with 95 % conversion and 86 % de.

Process for the reduction of carbonyl compounds

PCT No. PCT/JP97/00189 Sec. 371 Date Dec. 29, 1997 Sec. 102(e) Date Dec. 29, 1997 PCT Filed Jan. 29, 1997 PCT Pub. No. WO97/28105 PCT Pub. Date Aug. 7, 1997The present invention provides a process for reducing carbonyl compounds to hydroxy compounds, in particular stereoselectively reducing alpha -aminohaloketone derivatives, under mild conditions in an easy and simple manner, which comprises reacting a carbonyl compound of the general formula (1) with an organoaluminum compound of the general formula (4) to provide the corresponding alcohol compound of the general formula (5).

Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research

The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.