BOC-D-THR-OH Chemical Properties

Melting point:

81 °C

refractive index 

9 ° (C=1, AcOH)

storage temp. 

Sealed in dry,Room Temperature

solubility 

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

form 

Solid

color 

White to Almost white

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

55674-67-4(CAS DataBase Reference)

Safety Information

HS Code 

29225090

BOC-D-THR-OH Usage And Synthesis

Chemical Properties

White powder

Uses

It is known to inhibit growth and cell wall synthesis of Mycobacterium smegmatis. Also used as a synthetic intermediate for the production of chiral antibiotics.

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 (2S,3S)-2-amino-3-hydroxybutyric acid and di-tert-butyl dicarbonate is as follows: 1. di-tert-butyl dicarbonate (550 mg, 2.52 mmol) was added to a mixture of methanol (2.5 mL) and water (2.5 mL) containing L-isothreonine (250 mg, 2.10 mmol) and sodium bicarbonate (529 mg, 6.30 mmol) at 0 °C. 2. The reaction mixture was gradually warmed to room temperature and stirred continuously at room temperature for 18 hours. 3. Upon completion of the reaction, the methanol was removed by concentration and the remaining aqueous phase was adjusted to pH 3~4 with 6N hydrochloric acid solution. 4. The acidified aqueous phase was extracted with ether (3 times) and all organic phases were combined. 5. The organic phase was washed with water and brine sequentially, and then dried with anhydrous sodium sulfate. 6. The desiccant was removed by filtration, and the filtrate was concentrated under vacuum and further dried under vacuum for 24 h. (2R,3S)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutyric acid (304 mg) was obtained as a white solid. Product identification: LCMS retention time (Rt) = 0.36 min; mass spectrum (MS) m/z 220 [M + H]+, m/z 218 [M-H]-.

References

[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6935 - 6960
[2] Journal of the American Chemical Society, 2000, vol. 122, # 41, p. 10214 - 10215
[3] Journal of the American Chemical Society, 2003, vol. 125, # 7, p. 1877 - 1887
[4] Journal of Organic Chemistry, 1982, vol. 47, # 26, p. 5160 - 5167
[5] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 16, p. 4329 - 4332

BOC-D-THR-OH(55674-67-4)Related Product Information

• Boc-Thr(Bzl)-OH
• N-(tert-Butoxycarbonyl)-O-benzyl-D-threonine
• BOC-D-THR-OH
• BOC-L-THR-OH
• D-Threonine
• (R,S)-A-N-BOC-AMINO-B-HYDROXY-CYCLOHEXANEPROPANIC ACID
• N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID
• BOC-D-THR(TBU)-OH
• BOC-D-THREO-3-(FURAN-2-YL)SERINE
• BOC-D-THREO-3-(PYRIDIN-2-YL)SERINE
• BOC-D-THREO-3-PHENYLSERINE
• BOC-(2R,3S)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID
• BOC-D-THREO-3-(THIOPHEN-2-YL)SERINE
• BOC-CIS-3-HYDROXY-D-PROLINE
• Boc-allo-Thr-OH,BOC-ALLO-THR-OH DCHA
• BOC-D-THR(BZL)-O-CH2-PHI-CH2-COOH DCHA
• methyl (2R,3S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-(2-nitrophenyl)propanoate
• methyl (2R,3S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-(3-nitrophenyl)propanoate