T-Butyl (2S)-2-[(benzyloxycarbonylamino)]-4-hydroxybutyrate

Base Information

• Chemical Name: T-Butyl (2S)-2-[(benzyloxycarbonylamino)]-4-hydroxybutyrate
• CAS No.: 78266-81-6
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• DSSTox Substance ID: DTXSID50445200
• Nikkaji Number: J1.582.386K
• Wikidata: Q82263553
• Mol file: 78266-81-6.mol

Synonyms:78266-81-6;T-BUTYL (2S)-2-[(BENZYLOXYCARBONYLAMINO)]-4-HYDROXYBUTYRATE;(S)-tert-Butyl 2-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate;tert-butyl (2S)-4-hydroxy-2-(phenylmethoxycarbonylamino)butanoate;N-Cbz-L-homoserine tert-butyl ester;SCHEMBL376154;N-(Benzyloxycarbonyl)-L-homoserine tert-Butyl Ester;DTXSID50445200;AKOS015904579;AG-H-14083;CS-0312346;F80214;TERT-BUTYL ((BENZYLOXY)CARBONYL)-L-HOMOSERINATE;1,1-dimethyl-ethyl N-[(phenylmethoxy)carbonyl]-L-homoserinate;(S)-tert-Butyl2-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate;(S)-2-Benzyloxycarbonylamino-4-hydroxy-butyric Acid tert-butyl Ester

Chemical Property of T-Butyl (2S)-2-[(benzyloxycarbonylamino)]-4-hydroxybutyrate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 467.356°C at 760 mmHg
• Flash Point: 236.449°C
• PSA: 84.86000
• Density: 1.154g/cm³
• LogP: 2.39640
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Dichloromethane
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 358

Purity/Quality:

99%, ^*data from raw suppliers

t-Butyl(2S)-2-[(Benzyloxycarbonylamino)]-4-hydroxybutyrate ^*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)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CCO)NC(=O)OCC1=CC=CC=C1

Technology Process of T-Butyl (2S)-2-[(benzyloxycarbonylamino)]-4-hydroxybutyrate

There total 15 articles about T-Butyl (2S)-2-[(benzyloxycarbonylamino)]-4-hydroxybutyrate 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: 96.0%

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester (47307-26-6,149967-07-7) → tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate (78266-81-6)

Guidance literature:

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 0.166667h;

With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1002/ejoc.200900233

Reference yield: 79.0%

benzyl chloroformate (501-53-1,94274-21-2) + (S)-homoserine t-butyl ester (78266-80-5) → tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate (78266-81-6)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; In chloroform; for 5h; Ambient temperature;

DOI:10.1002/hlca.19830660424

Reference yield:

(S)-2-Benzyloxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid tert-butyl ester → tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate (78266-81-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; Ambient temperature;

DOI:10.1021/jo962257e

upstream raw materials:

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester

benzyl chloroformate

(S)-homoserine t-butyl ester

N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester

Downstream raw materials:

2(S)-2-(benzyloxycarbonylamino)-4-iodobutyric acid tert-butyl ester

tert-butyl (2S)-4-bromo-2-(N-benzyloxycarbonyl)aminobutyrate

C₄₃H₆₄N₂O₁₁S

C₆₅H₉₇N₃O₁₆S₂

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