100157-53-7

Basic information

• Product Name: (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)aMino)-3-hydroxybutanoate
• Synonyms: (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)aMino)-3-hydroxybutanoate;N-Cbz-D-allo-threonine Methyl Ester;(2R,3R)-Methyl 2-(((benzyloxy)carbonyl)aMino)-3-hydroxybutanoate
• CAS NO: 100157-53-7
• Molecular Formula: C₁₃H₁₇NO₅
• Molecular Weight: 267.27778
• Mol File: 100157-53-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)aMino)-3-hydroxybutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)aMino)-3-hydroxybutanoate(100157-53-7)
• EPA Substance Registry System: (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)aMino)-3-hydroxybutanoate(100157-53-7)

Safety Data

• Hazardous Substances Data: 100157-53-7(Hazardous Substances Data)

Usage

General Description

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate is a chemical compound with the molecular formula C15H19NO5. It is an ester derivative of the amino acid alanine and has a chiral center, making it optically active. The compound is commonly used in the synthesis of peptide-based drugs and as a reagent in organic chemistry. It is a white to off-white solid with a molecular weight of 297.31 g/mol and a melting point of around 73-75°C. The compound is also known by its synonyms such as N-Benzyloxycarbonyl-L-alanine methyl ester and Boc-L-Ala-OMe.

Upstream product

• 39994-75-7 H-DL-aThr-OMe*HCl 
• 501-53-1 benzyl chloroformate 
• 113479-92-8 2-Benzyloxycarbonylamino-4-oxo-pentanoic acid methyl ester 
• 39994-75-7 (+/-) threonine methyl ester hydrochloride 
• 198147-98-7 (2S,5S,6R)-6-Methyl-5-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-2-((R)-1-triisopropylsilanyloxy-ethyl)-[1,3]oxazinan-4-one 
• 67-56-1 methanol 
• 60538-18-3 (2R,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride 

Downstream Products

• 133957-12-7 N-Cbz-O-BOM-D-allo-threonine methyl ester 
• 60027-61-4 methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate 
• 119221-16-8 (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid 
• 838-85-7 diphenyl hydrogen phosphate 
• 93845-86-4 3-Benzhydryloxy-2-benzyloxycarbonylamino-butyric acid methyl ester 
• 113479-53-1 ((3R,5R)-5-Methyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester 
• 113479-53-1 ((3R,5S)-5-Methyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester 
• 133957-13-8 (2R,3R)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester 
• 134002-84-9 [(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester 
• 133957-15-0 [(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2S,6S)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester 
• 131057-58-4 N-carbobenzoxy-O-tert-butyldiphenylsilyl-D-allo-threoninal 
• 133957-14-9 [(1R,2R)-2-Benzyloxymethoxy-1-((2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester 
• 133957-14-9 [(1R,2R)-2-Benzyloxymethoxy-1-((2S,6S)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester 
• 133957-00-3 ((1R,2R)-2-Benzyloxymethoxy-1-formyl-propyl)-carbamic acid benzyl ester 

Relevant articles and documents

Hetero Diels-Alder vs Electrocyclic Reaction of Azadiene: Selective Synthesis of All Stereoisomers of Threonines

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γ-Lactam analogues of monocyclic β-lactam antibiotics

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Routes to Mitomycins. Chirospecific Synthesis of Aziridinomitosenes

The syntheses of ethyl (1R,2R)-1,2-(N-benzylaziridino)-7-methoxy-6-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrroloindole-9-carboxylate (59) and a regioisomeric aziridinoindoloquinone 60 are presented.Aziridine ring closure on a tricyclic indoloquinone nucleus and on monocyclic pyrrolidine derivatives was unsuccessful but did succeed with the acyclic educt.Thus the synthesis of the target aziridinomitosene was achieved by aziridine ring closure on the asymmetric 2-amino-3-hydroxy-4-azidobutanoate 49 followed by homologation and reductive ring closure to the bicyclic aziridinopyrrolidine 54.Subsequent reduction, regiospecific addition to 2,3-dibromo-5-methoxy-6-methylbenzoquinone (27), photochemical rearrangement, oxidation, and palladium-catalyzed ring closure afforded the (R,R)-aziridinomitosene 59.Regioisomeric aziridinoindoloquinone 60 was obtained directly by the addition of bicyclic aziridine 54 to dibromoquinone 27 followed by copper(II)-catalyzed ring closure.