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

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

Uses

Used in Pharmaceutical Industry:
(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate is used as a building block in the synthesis of peptide-based drugs for its ability to form stable peptide bonds and improve the pharmacokinetic properties of the final drug product.
Used in Organic Chemistry:
In the field of organic chemistry, (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate serves as a versatile reagent for various chemical reactions, including protection and deprotection of functional groups, and as a chiral auxiliary in asymmetric synthesis to induce enantioselectivity.
Used in Research and Development:
(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate is utilized in research and development for the study of peptide chemistry, drug discovery, and the development of novel synthetic methodologies. Its unique properties and reactivity make it a valuable tool for exploring new chemical space and advancing scientific understanding.

Upstream product

• 60538-18-3 (2R,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride 
• 501-53-1 benzyl chloroformate 
• 67-56-1 methanol 
• 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 
• 39994-75-7 H-DL-aThr-OMe*HCl 
• 113479-92-8 2-Benzyloxycarbonylamino-4-oxo-pentanoic acid methyl ester 
• 39994-75-7 (+/-) threonine methyl ester hydrochloride 

Downstream Products

• 60027-61-4 methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate 
• 101314-67-4 3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threonine methyl ester 
• 74112-78-0 3-O-(3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threonine methyl ester 
• 23141-51-7 3-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threonine methyl ester 
• 119221-16-8 (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid 
• 104160-29-4 Z-D-alloThr(OMe)OH 
• 100157-59-3 Z-N-Me-D-aThr(tBu)-L-Arg(NO₂)-OMe 
• 100157-56-0 Z-N-Me-D-aThr(tBu)-OH 
• 100157-55-9 Z-D-aThr(t-Bu)-OH 
• 133957-00-3 ((1R,2R)-2-Benzyloxymethoxy-1-formyl-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 
• 133957-14-9 [(1R,2R)-2-Benzyloxymethoxy-1-((2R,6R)-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 
• 133957-15-0 [(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2S,6S)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester 

Relevant articles and documents

HIGH-PRESSURE CYCLOADDITION OF 1-METHOXY-1,3-BUTADIENE TO N,O-PROTECTED D-THREONINALS AND D-ALLO-THREONINALS

High-pressure cycloadditions of trans-1-methoxy-1,3-butadiene (3) to N,O-protected D-allo-threoninals (4) and D-threoninals (8) were studied.In all cases, 5,6-syn-adducts were the major products.The results are explained by α-chelation with Eu(fod)3

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.