(2R,3R)-2-azaniumyl-3-hydroxybutanoate

Base Information

• Chemical Name: (2R,3R)-2-azaniumyl-3-hydroxybutanoate
• CAS No.: 24830-94-2
• Molecular Formula: C4H9NO3
• Molecular Weight: 119.12
• Hs Code.: 29225090
• Mol file: 24830-94-2.mol

Synonyms:(2R,3R)-2-azaniumyl-3-hydroxybutanoate;D-allothreonine zwitterion;CHEBI:58645

Chemical Property of (2R,3R)-2-azaniumyl-3-hydroxybutanoate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.77E-06mmHg at 25°C
• Melting Point: 276 °C (dec.)(lit.)
• Refractive Index: -10 ° (C=5, 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.: Water (Slightly)
• 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-allo-Threonine 99+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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(-)-allo-Threonine is an isomer of threonine. It is found as a constituent of an increasing group of biologically active peptides. Stereocontrolled syntheses of chiral and racemic key intermediates to thienamycin can be achieved from d-allo-threonine and trans-crotonic acid.
• Uses: They are found as constituents of an increasing group of biologically active peptides. Stereocontrolled syntheses of chiral and racemic key intermediates to thienamycin from d-allo-threonine and trans-crotonic acid.

Technology Process of (2R,3R)-2-azaniumyl-3-hydroxybutanoate

There total 114 articles about (2R,3R)-2-azaniumyl-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:

grassypeptolide A (1010433-25-6) → (R)-2-aminobutyric acid (2623-91-8) + D-allo-threonine (24830-94-2,134357-96-3,7013-32-3,82822-12-6) + N-methyl-L-valine (2480-23-1) + N-methyl-D-aspartate (6384-92-5) + L-Cysteic acid (498-40-8,3024-83-7) + D-Cysteic acid (35554-98-4,3024-83-7) + N-methyl-L-aspartic acid (4226-18-0) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

grassypeptolide A; With ozone; at 20 ℃; for 0.5h;

oxidative conditions;

DOI:10.1021/jo1013564

upstream raw materials:

rac-allo-threonine

N-methyl-threonine

2-Dibenzylamino-3-hydroxy-butyric acid

acetaldehyde

Downstream raw materials:

N-carbamoyl-threonine

acetaldehyde

acetic acid

butyric acid