100157-53-7 Usage
Description
(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate is a chiral ester derivative of the amino acid alanine with the molecular formula C15H19NO5. It is an optically active compound due to its chiral center and is commonly used in the synthesis of peptide-based drugs and as a reagent in organic chemistry. This white to off-white solid has a molecular weight of 297.31 g/mol and a melting point of approximately 73-75°C. It is also known by its synonyms N-Benzyloxycarbonyl-L-alanine methyl ester and Boc-L-Ala-OMe.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 100157-53-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,1,5 and 7 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 100157-53:
(8*1)+(7*0)+(6*0)+(5*1)+(4*5)+(3*7)+(2*5)+(1*3)=67
67 % 10 = 7
So 100157-53-7 is a valid CAS Registry Number.
100157-53-7Relevant articles and documents
Hetero Diels-Alder vs Electrocyclic Reaction of Azadiene: Selective Synthesis of All Stereoisomers of Threonines
Bongini, Alessandro,Panunzio, Mauro,Bandini, Elisa,Martelli, Giorgio,Spunta, Giuseppe
, p. 8911 - 8913 (2007/10/03)
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γ-Lactam analogues of monocyclic β-lactam antibiotics
Crossley,Crumbie,Fung,et al.
, p. 2883 - 2886 (2007/10/02)
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Routes to Mitomycins. Chirospecific Synthesis of Aziridinomitosenes
Shaw, Kenneth J.,Luly, Jay R.,Rapoport, Henry
, p. 4515 - 4523 (2007/10/02)
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.