(2S,3R)-tert-Butyl 2-amino-3-(tert-butoxy)butanoate

Base Information

• Chemical Name: (2S,3R)-tert-Butyl 2-amino-3-(tert-butoxy)butanoate
• CAS No.: 5854-78-4
• Molecular Formula: C12H25NO3
• Molecular Weight: 231.335
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID50427041
• Nikkaji Number: J215.735G
• Wikidata: Q72504344
• Mol file: 5854-78-4.mol

Synonyms:5854-78-4;H-Thr(tBu)-OtBu;O-tert-Butyl-L-threonine tert-Butyl Ester;(2S,3R)-tert-Butyl 2-amino-3-(tert-butoxy)butanoate;O-tert-Butylthreoninetert-butyl ester;tert-butyl (2S,3R)-2-amino-3-[(2-methylpropan-2-yl)oxy]butanoate;L-Threonine, O-(1,1-dimethylethyl)-, 1,1-dimethylethyl ester;TERT-BUTYL (2S,3R)-2-AMINO-3-(TERT-BUTOXY)BUTANOATE;O-tert-Butyl-L-threonine-tert-butyl ester;MFCD00077109;L-Thr(tBu)-OtBu;SCHEMBL918459;DTXSID50427041;PPDIUNOGUIAFLV-BDAKNGLRSA-N;TD8072;AKOS015838085;AKOS015998991;tert-Butyl O-tert-butyl-L-threoninate;CS-W010364;DS-1904;HY-W009648;O-tert-Butyl-L-threonine tert-Butyl Este;B3340;EN300-1165872;(2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate;2-Methyl-2-propanyl O-(2-methyl-2-propanyl)-L-threoninate;O-(1,1-Dimethylethyl)-L-threonine 1,1-dimethylethyl ester

Chemical Property of (2S,3R)-tert-Butyl 2-amino-3-(tert-butoxy)butanoate

Chemical Property:

• Vapor Pressure: 0.00146mmHg at 25°C
• Melting Point: 74-75 °C
• Refractive Index: 1.448
• Boiling Point: 296.1 °C at 760 mmHg
• PKA: 6.14±0.33(Predicted)
• Flash Point: 79.3 °C
• PSA: 61.55000
• Density: 0.959 g/cm³
• LogP: 2.55930
• Storage Temp.: -15°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 231.18344366
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

99.0% ^*data from raw suppliers

O-tert-Butyl-L-threonine tert-butyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)OC(C)(C)C)N)OC(C)(C)C
• Isomeric SMILES: C[C@H]([C@@H](C(=O)OC(C)(C)C)N)OC(C)(C)C
• Uses: O-tert-Butylthreonine tert-Butyl Ester, can be used in the synthesis of various chemical compounds having therapeutic activity, such as N-[[[(1S)-1-[3-(2-Pyrazinyl)-1,2,4-oxadiazol-5-yl]-3-butyn-1-yl]amino]carbonyl]-L-threonine (P842605), used as immune modeulators.

Technology Process of (2S,3R)-tert-Butyl 2-amino-3-(tert-butoxy)butanoate

There total 6 articles about (2S,3R)-tert-Butyl 2-amino-3-(tert-butoxy)butanoate 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: 67.2%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + isobutene (115-11-7,15220-85-6) → (2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate (5854-78-4)

Guidance literature:

L-threonine; With trifluorormethanesulfonic acid; In 1,2-dimethoxyethane; at -10 - 5 ℃;

isobutene; In 1,2-dimethoxyethane; at -15 - -10 ℃; for 48h; Reagent/catalyst; Solvent;

Reference yield: 30.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + tert-butyl methyl ether (1634-04-4) → (2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate (5854-78-4)

Guidance literature:

With sulfuric acid; at 25 ℃; for 2h; chemoselective reaction; Molecular sieve;

DOI:10.1016/j.tetlet.2011.11.108

Reference yield:

N-Carbobenzoxy-O-tert.-butyl-L-threonin-tert.-butylester (14437-51-5) → (2S,3R)-tert-butyl 2-amino-3-tert-butoxybutanoate (5854-78-4)

Guidance literature:

With hydrogen; palladium; In methanol;

upstream raw materials:

N-Carbobenzoxy-O-tert.-butyl-L-threonin-tert.-butylester

N-benzyloxycarbonyl-L-treonine

isobutene

L-threonine

Downstream raw materials:

o-nitrophenylsulfenyl-O-tert-butyl-L-threonine tert-butyl ester

Z-Thr(t-Bu)-Thr(t-Bu)-O(t-Bu)

1-phenylbutan-1,3-dione

Refernces

• 1、 -. "Preparation method of O-tert-butyl-L-threonine tert-butyl ester". Paragraph 0028; 0029; 0030; 0031; 0032; 0033; 0034-0047. . Retrieved 2017/08/27.
• 2、 -. "METHOD FOR THE MANUFACTURE OF L-THREONINE-O-(1,1-DIMETHYLETHYL)-1,1-DIMETHYLETHYL ESTER". Page/Page column 5. . Retrieved 2008/06/13.