(S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Base Information

• Chemical Name: (S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate
• CAS No.: 79069-16-2
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• DSSTox Substance ID: DTXSID601142059
• Mol file: 79069-16-2.mol

Synonyms:(S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate;79069-16-2;Benzyl (3S)-4-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;SCHEMBL1262680;XEGSFNZVTUGZCK-ZDUSSCGKSA-N;DTXSID601142059;AMY24011;Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-,phenylmethyl ester, (3S)-;C16382;A864926;benzyl (s)-3-(t-butoxycarbonylamino)-4-hydroxybutanoate;(S)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxybutanoate;(S)-benzyl3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate;benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate;benzyl (3S)-3-[(tert-butoxycarbonyl)amino]4 hydroxybutanoate;(S)-3-t-butoxycarbonylamino-4-hydroxy-butyric acid benzyl ester;(S)-3-tert-butoxycarbonylamino-4-hydroxy-butyric acid benzyl ester;tert-butyl (S)-1-((benzyloxy)carbonyl)-3-hydroxypropan-2-ylcarbamate;Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

Chemical Property of (S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Chemical Property:

• Melting Point: 57 °C(Solv: ethyl acetate (141-78-6); cyclohexane (110-82-7))
• Boiling Point: 467.4±45.0 °C(Predicted)
• PKA: 11.53±0.46(Predicted)
• PSA: 84.86000
• Density: 1.154±0.06 g/cm3(Predicted)
• LogP: 2.39640
• 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:

97% ^*data from raw suppliers

(S)-Benzyl3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate 97% ^*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(CC(=O)OCC1=CC=CC=C1)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(=O)OCC1=CC=CC=C1)CO

Technology Process of (S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

There total 16 articles about (S)-benzyl 3-((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: 95.0%

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate (79069-16-2)

Guidance literature:

DOI:10.1002/(SICI)1521-3773(19980216)37:3<302::AID-ANIE302>3.0.CO;2-4

Reference yield:

(S)-3-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester (84890-97-1) → benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate (79069-16-2)

Guidance literature:

With sodium tetrahydroborate; In 1,2-dimethoxyethane; water; at -15 ℃; for 0.00833333h; Yield given;

DOI:10.1016/S0040-4039(00)92121-X

Reference yield:

4-(phenylmethyl) N-[(1,1-dimethylethoxy)carbonyl]-1(2,5-dioxo-1-pyrrolidinyl) L-aspartate (118943-18-3) → benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate (79069-16-2)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; at -5 - 15 ℃; for 0.75h;

upstream raw materials:

BOC-L-aspartic acid 4-benzyl ester

(S)-3-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester

di-tert-butyl dicarbonate

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid

Downstream raw materials:

benzyl (S)-2-(N-t-butoxycarbonylamino)-4-iodobutanoate

(S)-3-tert-Butoxycarbonylamino-4-(6-chloro-purin-9-yl)-butyric acid benzyl ester

(S)-N-[(tert-butoxy)carbonyl]-γ-(3-benzoylthymin-1-yl)-β-homoalanine benzyl ester

(S)-N-[(tert-butoxy)carbonyl]-γ-(2-amino-6-chloropurin-9-yl)-β-homoalanin benzyl ester

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR MODULAR CONTROL OF BIOORTHOGONAL LIGATION". Page/Page column 72; 74. . Retrieved 2020/06/19.
• 2、 Kumar, Pratik,Jiang, Ting,Zainul, Omar,Preston, Alyssa N.,Li, Sining,Farr, Joshua D.,Suri, Pavit,Laughlin, Scott T.. "Lipidated cyclopropenes via a stable 3-N spirocyclopropene scaffold". . p. 3435 - 3438. Retrieved 2018/08/21.