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

Base Information

• Chemical Name: (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate
• CAS No.: 81323-58-2
• Molecular Formula: C13H25NO5
• Molecular Weight: 275.345
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID40453576
• Nikkaji Number: J911.008I
• Wikidata: Q82274742
• Mol file: 81323-58-2.mol

Synonyms:81323-58-2;(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate;tert-butyl (tert-butoxycarbonyl)-L-homoserinate;N-Boc-L-Homoserine tert-butyl ester;Tert-butyl (2S)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;SCHEMBL1343403;BOC-L-homoserine t-butyl ester;DTXSID40453576;(S)-tert-Butyl2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate;MFCD08275190;AM85393;EX-A3316-1;BS-25939;NW-09-15-1;A847244;tert-Butyl N-(tert-butoxycarbonyl)-L-homoserinate;n-(tert-butyloxycarbonyl)-(s)-homoserine tert-butyl ester;t-butyl (2S)-2-(tert-butoxycarbonylamino)-4-hydroxybutanoate

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

Chemical Property:

• Boiling Point: 393.353 °C at 760 mmHg
• PKA: 10.91±0.46(Predicted)
• Flash Point: 191.693 °C
• PSA: 84.86000
• Density: 1.072 g/cm³
• LogP: 1.99470
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 275.17327290
• Heavy Atom Count: 19
• Complexity: 314

Purity/Quality:

98% ^*data from raw suppliers

N-(tert-Butoxycarbonyl)-(S)-homoserinetert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 18 articles about (S)-tert-Butyl 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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-tert-butyl 2-[N-(9-(9-phenylfluorenyl))amino]-4-hydroxybutanoate (215182-75-5) → N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester (81323-58-2)

Guidance literature:

With palladium dihydroxide; hydrogen; In tetrahydrofuran; for 48h; under 3800.26 Torr;

DOI:10.3987/COM-08-S(N)69

Reference yield: 95.0%

N-tert-butoxycarbonyl aspartic acid tert-butyl ester (34582-32-6) → N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester (81323-58-2)

Guidance literature:

N-tert-butoxycarbonyl aspartic acid tert-butyl ester; With 4-methyl-morpholine; isobutyl chloroformate; In 1,2-dimethoxyethane; at -15 ℃; for 0.166667h;

With sodium tetrahydroborate; water; In 1,2-dimethoxyethane; at -15 ℃; for 0.0833333h;

Reference yield: 44.0%

L-homoserine (672-15-1,119736-88-8) + tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester (81323-58-2)

Guidance literature:

L-homoserine; di-tert-butyl dicarbonate; With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

tert-Butyl 2,2,2-trichloroacetimidate; In tetrahydrofuran; dichloromethane; at 20 ℃;

DOI:10.1039/d1ob01715b

upstream raw materials:

N-tert-butoxycarbonyl aspartic acid tert-butyl ester

di-tert-butyl dicarbonate

N-(diphenylmethylene)glycine tert-butyl ester

prenyl bromide

Downstream raw materials:

tert-butyl (2S)-azetidine-2-carboxylate

Refernces

• 1、 -. "NOVEL HISTONE METHYLTRANSFERASE INHIBITORS". . . Retrieved 2021/04/01.
• 2、 Bierer, Donald,Cui, Ji-Bin,Li, Yi-Ming,Shi, Jing,Wei, Xiao-Xiong,Zhao, Rui,Zhu, Huixia. "Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids". supporting information. p. 9021 - 9025. Retrieved 2021/11/04.