Boc-L-Threonine Chemical Properties

Melting point:

80-82 °C(lit.)

Boiling point:

360.05°C (rough estimate)

alpha 

-8.5 º (c=1, acetic acid)

Density 

1.2470 (rough estimate)

refractive index 

-7 ° (C=1, AcOH)

storage temp. 

-20°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.60±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

[α]20/D 8.5±1°, c = 1% in acetic acid

BRN 

2331474

InChI

InChI=1S/C9H17NO5/c1-5(11)6(7(12)13)10-8(14)15-9(2,3)4/h5-6,11H,1-4H3,(H,10,14)(H,12,13)/t5-,6+/m1/s1

InChIKey

LLHOYOCAAURYRL-RITPCOANSA-N

SMILES

C(O)(=O)[C@H]([C@H](O)C)NC(OC(C)(C)C)=O

CAS DataBase Reference

2592-18-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

HS Code 

29241990

MSDS

• Language:English Provider:Boc-L-Threonine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Boc-L-Threonine Usage And Synthesis

Chemical Properties

WHITE AMORPHOUS POWDER

Uses

N-Boc-L-threonine is an N-Boc-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).

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutyric acid from L-threonine and di-tert-butyl dicarbonate was as follows: 1. To a methanol (5 mL) solution of L-threonine (400 mg, 3.36 mmol), a water (5 mL) solution of sodium bicarbonate (434 mg, 5.17 mmol) was added, followed by di-tert-butyl dicarbonate (1.07 g, 4.90 mmol). 2. The reaction mixture was stirred at room temperature for 3 days. 3. Upon completion of the reaction, the solvent was removed by vacuum distillation. 4. 4. The residue was diluted with water (20 mL) and washed with ether (2 x 20 mL). 5. The aqueous layer was acidified with saturated aqueous sodium bisulfite and then extracted with 2-methyltetrahydrofuran. 6. The organic layer was dried over anhydrous sodium sulfate and subsequently concentrated in vacuo to afford the title compound (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutyric acid as a white solid (730 mg, 99% yield). 7. The product was characterized by 1H NMR (400 MHz, CDCl3) and LC-MS: 1H NMR δ 1.24 (d, 3H), 1.44 (s, 9H), 4.26 (d, 1H), 4.40 (d, 1H), 5.52 (d, 1H), 5.69 (br s, 1H); LCMS Rt = 1.68 min, MS m/z 218 [M + H]+.

References

[1] Patent: WO2013/114250, 2013, A1. Location in patent: Page/Page column 161; 162
[2] Patent: WO2013/110643, 2013, A1. Location in patent: Paragraph 00118; 00119
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1795 - 1802
[4] Patent: CN102993200, 2016, B. Location in patent: Paragraph 0043; 0044; 0045
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5770 - 5781

Boc-L-Threonine(2592-18-9)Related Product Information

• L-Threonine
• N-Carbobenzyloxyglycine
• tert-Butyl carbazate
• DI-TERT-BUTYL ETHER
• BOC-THR(ME)-OH
• N-tert-Butyloxycarbonyl-N-methyl-O-benzyl-L-threonine
• Boc-Thr(Bzl)-OH
• Boc-O-tert-butyl-L-threonine
• BOC-D-THREONINE(BZL)-OH
• BOC-D-THREONINE extrapure,N-ALPHA-T-BOC-D-THREONINE / (2R,3S),N-ALPHA-T-BOC-D-THREONINE,BOC-D-THREONINE
• BOC-L-THR(BZL)-O-CH2-PHI-CH2-COOH DCHA
• BOC-THR(P-CHLORO-BZL)-OH DCHA
• N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID
• BOC-L-THREONINE DCHA
• tert-butyl [R-(R*,S*)]-[1-[[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl]-2-hydroxypropyl]carbamate
• BOC-THR(BZL)-ONP
• Methyl N-(tert-butoxycarbonyl)-L-threoninate
• BPOC-THR(TBU)-OSU