(S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

Base Information

• Chemical Name: (S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate
• CAS No.: 146398-02-9
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90567415
• Nikkaji Number: J2.301.367C
• Wikidata: Q82453304
• Mol file: 146398-02-9.mol

Synonyms:146398-02-9;(S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate;tert-butyl (3S)-4-hydroxy-3-(phenylmethoxycarbonylamino)butanoate;tert-butyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoate;Butanoic acid, 4-hydroxy-3-[[(phenylMethoxy)carbonyl]aMino]-,1,1-diMethylethyl ester, (3S)-;IVQADIBBXAAFHJ-ZDUSSCGKSA-N;SCHEMBL5197783;DTXSID90567415;E87372;N-benzyloxycarbonyl-3(S)-hydroxymethyl beta-alanine tert-butyl ester;tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoate;N(benzyloxycarbonyl)-3(S)-hydroxymethyl-beta-alanine tert-butyl ester;N-(benzyloxycarbonyl)-3(S)-hydroxymethyl-beta-alanine tert-butyl ester;n-benzyloxycarbonyl-3(s)-hydroxymethyl -beta-alanine tert-butyl ester

Chemical Property of (S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

Chemical Property:

• Boiling Point: 467.4±45.0 °C(Predicted)
• PKA: 11.33±0.46(Predicted)
• PSA: 88.35000
• Density: 1.154±0.06 g/cm3(Predicted)
• LogP: 2.20990
• XLogP3: 1.6
• 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:

98%min ^*data from raw suppliers

(S)-TERT-BUTYL-3-(((BENZYLOXY)CARBONYL)AMINO)-4-HYDROXYBUTANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(CO)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@@H](CO)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

There total 9 articles about (S)-tert-Butyl 3-(((benzyloxy)carbonyl)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: 95.0%

Z-D(tBu)-OH (5545-52-8) → tert-butyl (S)-3-benzyloxycarbonylamino-4-hydroxybutyrate (146398-02-9)

Guidance literature:

With 4-methyl-morpholine; sodium tetrahydroborate; isobutyl chloroformate; In tetrahydrofuran; at -78 ℃; for 0.333333h;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1960::AID-HLCA1960>3.0.CO;2-2

Reference yield: 81.0%

→ tert-butyl (S)-3-benzyloxycarbonylamino-4-hydroxybutyrate (146398-02-9)

Guidance literature:

Reference yield: 26.0%

3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester (169498-46-8) → tert-butyl (S)-3-benzyloxycarbonylamino-4-hydroxybutyrate (146398-02-9) + (2R)-2-tert-butoxycarbonylmethyl-aziridine-1-carboxylic acid benzyl ester (668475-45-4)

Guidance literature:

With (n-Hex)CuCNLi₂; In tetrahydrofuran; at -40 ℃;

DOI:10.1016/j.tetlet.2007.04.108

upstream raw materials:

Z-D(tBu)-OH

Z-Asp(OtBu)-OSu

(S)-3-Benzyloxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid tert-butyl ester

3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester

Downstream raw materials:

(3S)-3-(benzyloxycarbonylamino)-4-(p-toluenesulfonyloxy)-butanoic acid t-butyl ester

(S)-4-oxo-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

3-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid tert-butyl ester

(2R)-2-tert-butoxycarbonylmethyl-aziridine-1-carboxylic acid benzyl ester