Boc-Thr(Bzl)-OH Chemical Properties

Melting point:

80-82 °C(lit.)

alpha 

22 º (c=2 in 95% ethanol)

Boiling point:

461.5±45.0 °C(Predicted)

Density 

1.152±0.06 g/cm3(Predicted)

refractive index 

16.5 ° (C=1, MeOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

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

pka

3.50±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

[α]20/D +16.5±1°, c = 1% in methanol

BRN 

3065591

InChI

InChI=1S/C16H23NO5/c1-11(21-10-12-8-6-5-7-9-12)13(14(18)19)17-15(20)22-16(2,3)4/h5-9,11,13H,10H2,1-4H3,(H,17,20)(H,18,19)/t11-,13+/m1/s1

InChIKey

CTXPLTPDOISPTE-YPMHNXCESA-N

SMILES

C(O)(=O)[C@H]([C@H](OCC1=CC=CC=C1)C)NC(OC(C)(C)C)=O

CAS DataBase Reference

15260-10-3(CAS DataBase Reference)

EPA Substance Registry System

L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- (15260-10-3)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

2924 29 70

MSDS

• Language:English Provider:N-tert-Butoxycarbonyl-O-benzyl-L-threonine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Boc-Thr(Bzl)-OH Usage And Synthesis

Chemical Properties

White crystalline

Uses

Boc-O-benzyl-L-threonine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Application

Boc-Thr(Bzl)-OH is a standard building block for introduction of threonine amino-acid residues by Boc SPPS.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

To a stirred solution of (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoic acid (250 g, 1.44 mol) in DMF (1 L) was added 60% sodium hydride (68 g, 2.85 mol) in batches at -20 °C and protected by nitrogen and stirring was continued for 2 hours. Subsequently, benzyl bromide (167 mL, 1.36 mol) was slowly added dropwise and the reaction mixture was continued to be stirred at room temperature for 3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming complete consumption of the raw materials, the reaction was quenched with ice water and subsequently washed with ether (2 x 250 mL). The aqueous layer was separated and the pH was adjusted to about 2 with citric acid solution, followed by extraction with ethyl acetate (2 x 300 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford (2S,3R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid (320 g, 90% yield) as a thick paste.1H-NMR (500 MHz, DMSO-d6) data: δ 12.64 (broad single peak, 1H), 7.34-7.25 (multiple peaks, 5H), and 6.46 (double peak, J=8.5Hz, 1H), 4.53 (double peak, J=11.5Hz, 1H), 4.39 (double peak, J=12.0Hz, 1H), 4.00-3.98 (multiple peaks, 2H), 1.39 (single peak, 9H), 1.15 (double peak, J=6.0Hz, 3H).

References

[1] Patent: WO2018/26763, 2018, A1. Location in patent: Page/Page column 63
[2] Patent: WO2014/120786, 2014, A1. Location in patent: Paragraph 0101
[3] Patent: WO2014/120783, 2014, A1. Location in patent: Paragraph 0093
[4] Patent: WO2017/195069, 2017, A1. Location in patent: Page/Page column 66
[5] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 5, p. 1369 - 1377

Boc-Thr(Bzl)-OH(15260-10-3)Related Product Information

• tert-Butyl peroxyacetate
• tert-Butanol
• L-Threonine
• Benzyl chloride
• Benzyl benzoate
• Benzyl alcohol
• Benzyl isocyanate
• Benzyl nicotinate
• Benzyl
• N-tert-Butyloxycarbonyl-N-methyl-O-benzyl-L-threonine
• N-ALPHA-T-BOC-O-BENZYL-D-THREONINE / (2R,3S),N-ALPHA-T-BOC-O-BENZYL-D-THREONINE,BOC-O-BENZYL-D-THREONINE
• Boc-L-Threonine
• BOC-THR(P-CHLORO-BZL)-OH DCHA
• BOC-L-THR(BZL)-O-CH2-PHI-CH2-COOH DCHA
• BOC-O-BENZYL-L-THREONINE N-CARBOXY ANHYDRIDE
• BOC-O-BENZYL-L-THREONINE P-NITROPHENYL ESTER,BOC-O-BENZYL-L-THREONINE 4-NITROPHENYL ESTER
• BOC-THR(BZL)-OSU
• BOC-O-BENZYL-D-THREONINE 4-OXYMETHYLPHENYLACETAMIDOMETHYL RESIN,BOC-O-BENZYL-D-THREONINE MERRIFIELD RESIN