(S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Base Information

• Chemical Name: (S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate
• CAS No.: 120042-11-7
• Molecular Formula: C10H19 N O5
• Molecular Weight: 233.265
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID90441781
• Wikidata: Q82258718
• Mol file: 120042-11-7.mol

Synonyms:120042-11-7;N-BOC-L-HOMOSERINE METHYL ESTER;(S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate;methyl (2S)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;Homoserine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester;Methyl N-(tert-butoxycarbonyl)-L-homoserinate;MFCD09835542;S)-2-(tert-Butoxycarbonylamino)-4-hydroxybutyric Acid Methyl Este;N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine Methyl Ester;(S)-METHYL2-((TERT-BUTOXYCARBONYL)AMINO)-4-HYDROXYBUTANOATE;N-Boc homoserine methyl ester;SCHEMBL1837430;DTXSID90441781;IWNVPOPPBRMFNG-ZETCQYMHSA-N;AKOS016006755;FS-6155;CS-0088997;F15045;METHYL (TERT-BUTOXYCARBONYL)HOMOSERINATE;N-tert-butoxycarbonyl-L-homoserine Methyl Ester;A847245;Methyl N-{[(2-methyl-2-propanyl)oxy]carbonyl}homoserinate;L-Homoserine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester;(S)-(tert-butoxycarbonylamino)-4-hydroxybutyric acid methyl ester;(S)-2-tert-butoxycarbonylamino-4-hydroxy-butyric acid methyl ester;methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-hydroxybutanoate

Chemical Property of (S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Chemical Property:

• Boiling Point: 364.6±37.0 °C(Predicted)
• PKA: 10.91±0.46(Predicted)
• PSA: 88.35000
• Density: 1.125±0.06 g/cm3(Predicted)
• LogP: 0.63950
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 233.12632271
• Heavy Atom Count: 16
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-L-homoserineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCO)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCO)C(=O)OC

Technology Process of (S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

There total 20 articles about (S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid (41088-86-2) + methyl iodide (74-88-4) → methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate (120042-11-7,258351-86-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield: 83.0%

→ methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate (120042-11-7,258351-86-9)

Guidance literature:

Reference yield: 70.0%

α-methyl N-(tert-butoxycarbonyl)aspartate (98045-03-5,137130-65-5) + isobutyl chloroformate (543-27-1) → methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate (120042-11-7,258351-86-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -5 ℃; for 0.5h;

upstream raw materials:

tert-Butoxycarbonyl-L-homoserine DCHA salt

methyl iodide

α-methyl N-(tert-butoxycarbonyl)aspartate

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

Downstream raw materials:

methyl (2S)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid di-tert-butyl ester

(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester

Refernces

• 1、 Mann, Guy,Satish, Gandhesiri,Sulkshane, Prasad,Mandal, Shaswati,Glickman, Michael H.,Brik, Ashraf. "Synthesis and delivery of a stable phosphorylated ubiquitin probe to study ubiquitin conjugation in mitophagy". . p. 9438 - 9441. Retrieved 2021/09/22.
• 2、 Fankhauser, Daniel,Alissandratos, Apostolos,Liutkus, Mantas,Easton, Christopher J.. "Easy Production of “Difficult Peptides” Using Cell-Free Protein Synthesis and a New Methionine Analogue as a Latent Peptide Cleavage Site". supporting information. p. 17487 - 17494. Retrieved 2021/11/03.