(2R,3S)-2-amino-3-hydroxybutanoate

Base Information

• Chemical Name: (2R,3S)-2-amino-3-hydroxybutanoate
• CAS No.: 632-20-2
• Molecular Formula: C4H9NO3
• Molecular Weight: 119.12
• Hs Code.: 29225000
• Mol file: 632-20-2.mol

Synonyms:D-thr;(2R,3S)-2-amino-3-hydroxybutanoate;D-threonine zwitterion;CHEBI:57757

Chemical Property of (2R,3S)-2-amino-3-hydroxybutanoate

Chemical Property:

• Appearance/Colour: white crystalline powder or crystals
• Melting Point: 274 °C
• Refractive Index: 28 ° (C=3, H2O)
• Boiling Point: 345.8 °C at 760 mmHg
• PKA: 2.19±0.10(Predicted)
• Flash Point: 162.9 °C
• PSA: 83.55000
• Density: 1.307 g/cm³
• LogP: -0.52060
• Storage Temp.: Store at RT.
• Solubility.: H2O: soluble
• Water Solubility.: soluble
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 119.058243149
• Heavy Atom Count: 8
• Complexity: 87.8

Purity/Quality:

99% ^*data from raw suppliers

D-Threonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)[O-])[NH3+])O
• Isomeric SMILES: C[C@@H]([C@H](C(=O)[O-])[NH3+])O
• Description: D-threonine is the D-form of threonine, which is a kind of amino acids. It can be used for the preparation of enantiomerically pure 1, 3-butanediol. It is also used as the intermediate during the preparation of chiral compounds such as antibiotics. D-threonine is an effective chiral pool reagent which contains an extra stereo-center. For example, people has recently used it as the starting material for total synthesis of protected legionaminic acid.
• Uses: D-Threonine is the unnatural isomer of L-Threonine (T405500) and is known to inhibit growth and cell wall synthesis of Mycobacterium smegmatis. D-Threonine is also used as a synthetic intermediate for the production of chiral antibiotics. A steroisomer of the proteinogenic amino acid L-threonine.

Technology Process of (2R,3S)-2-amino-3-hydroxybutanoate

There total 108 articles about (2R,3S)-2-amino-3-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: 92.0%

2-amino-3-hydroxybutyronitrile (344328-90-1) → DL-threonine (72-19-5,80-68-2,144-98-9,632-20-2,2676-21-3,7004-04-8,24830-94-2,28954-12-3,36676-50-3,134357-96-3,7013-32-3,82822-12-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; ammonium hydroxide; In water; at 150 ℃; for 5h; under 22502.3 Torr; Autoclave; Inert atmosphere;

Reference yield: 89.4%

DL-5-(2-hydroxyethyl)hydantoin (64420-00-4) → DL-threonine (72-19-5,80-68-2,144-98-9,632-20-2,2676-21-3,7004-04-8,24830-94-2,28954-12-3,36676-50-3,134357-96-3,7013-32-3,82822-12-6)

Guidance literature:

DL-5-(2-hydroxyethyl)hydantoin; With calcium hydroxide; ammonia; In water; butan-1-ol; at 160 - 170 ℃; for 4h; under 11251.1 - 15001.5 Torr;

With carbon dioxide; In water; butan-1-ol; at 20 ℃; pH=8;

Reference yield:

callipeltin N → D-Alanine (338-69-2,25191-17-7,18875-37-1) + D-Threonine (632-20-2,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + D-arginine (157-06-2,25212-18-4) + pipecolinic acid (3105-95-1,83680-83-5)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 24h;

DOI:10.1016/j.tet.2016.09.016

upstream raw materials:

rac-allo-threonine

(R^*,R^*)-2-bromo-3-hydroxybutanoic acid

(+/-)-erythro-2-bromo-3-methoxy-butyric acid

N-formyl-O-methyl-D^s-threonine

Downstream raw materials:

(+/-) threonine methyl ester hydrochloride

allo-Thr-OMe

H-DL-aThr-OMe*HCl

N-carbamoyl-threonine

Refernces

• 1、 Wan, Xinhua,Wang, Zhaoxu,Ye, Xichong,Zhang, Jie. "Noncovalently Functionalized Commodity Polymers as Tailor-Made Additives for Stereoselective Crystallization". supporting information. p. 20243 - 20248. Retrieved 2021/08/09.
• 2、 Goto, Masaru,Hemmi, Hisashi,Ito, Tomokazu,Matsuoka, Mai,Matsushita, Kazuma,Mizobuchi, Taichi,Nasu, Ryoma,Watanabe, Soichiro,Yoshimura, Tohru. "Mechanism of eukaryotic serine racemase-catalyzed serine dehydration". . . Retrieved 2020/06/08.