(2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate

Base Information

• Chemical Name: (2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate
• CAS No.: 19728-63-3
• Molecular Formula: C12H15NO5
• Molecular Weight: 253.255
• Hs Code.: 29242990
• European Community (EC) Number: 243-258-1
• Mol file: 19728-63-3.mol

Synonyms:19728-63-3;NS00026411

Chemical Property of (2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder powder
• Vapor Pressure: 3.7E-11mmHg at 25°C
• Melting Point: 101-103 °C(lit.)
• Refractive Index: -4.9 ° (C=2, AcOH)
• Boiling Point: 483.7 °C at 760 mmHg
• PKA: 3.58±0.10(Predicted)
• Flash Point: 246.3 °C
• PSA: 95.86000
• Density: 1.309 g/cm³
• LogP: 1.13770
• Storage Temp.: −20°C
• Solubility.: almost transparency in Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 252.08719755
• Heavy Atom Count: 18
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

Z-L-Thr-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(C(=O)[O-])NC(=O)OCC1=CC=CC=C1)O
• Isomeric SMILES: C[C@H]([C@@H](C(=O)[O-])NC(=O)OCC1=CC=CC=C1)O
• Uses: N-Cbz-L-threonine is an N-Cbz-protected form of L-Threonine (T405500). L-Threonine is an essential amino acid that is commonly used as a feed and food additive. L-Threonine is produced in mass quantities by mutant Escherichia coli strains for research and food nutrition purposes. L-Threonine can be naturally found in fish and poultry, and is incorporated in some important proteins in the human body (such as hemoglobin and insulin).

Technology Process of (2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate

There total 26 articles about (2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)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: 99.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-L-treonine (19728-63-3)

Guidance literature:

With sodium hydroxide; at 0 ℃; for 1h;

DOI:10.1021/ja00251a021

Reference yield: 96.0%

N-benzyloxycarbonyl-O-t-butyl-L-threonine (16966-09-9) → N-benzyloxycarbonyl-L-treonine (19728-63-3)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; for 0.333333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79116-7

Reference yield: 93.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + Z-OSu → N-benzyloxycarbonyl-L-treonine (19728-63-3)

Guidance literature:

With sodium carbonate; In acetone; at 28 ℃; for 5h; Temperature; Cooling with ice;

upstream raw materials:

D-threonine

benzyl chloroformate

L-threonine

dibenzyl dicarbonate

Downstream raw materials:

N-benzyloxycarbonyl-O-chloroacetyl-threonine

DL-trans-5-Methyl-2-oxo-oxazolidin-4-carbonsaeure

N-benzyloxycarbonyl-DL-threonine benzyl ester

benzyl N-(benzyloxycarbonyl)-D,L-allothreoninate

Refernces

• 1、 -. "EP300/CREBBP INHIBITOR". Paragraph 0233; 0234; 0287; 0288. . Retrieved 2020/05/30.
• 2、 Kobayashi, Naotake,Sato, Norihito,Sugita, Katsuji,Takahashi, Kouji,Sugawara, Tamio,Tada, Yukio,Yoshikawa, Takayoshi. "Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate". . . Retrieved 2019/11/20.