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BOC-D-TYR(ME)-OH

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BOC-D-TYR(ME)-OH Basic information

Product Name:
BOC-D-TYR(ME)-OH
Synonyms:
  • (R)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID
  • N-ALPHA-T-BUTOXYCARBONYL-4-METHOXY-D-PHENYLALANINE
  • (2R)-3-(4-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  • Boc-O-methyl-D-tyrosine≥ 98% (HPLC)
  • Boc-π-methoxy-D-Phe-OH
  • N-ALPHA-T-BOC-O-METHYL-D-TYROSINE
  • N-ALPHA-T-BOC-P-METHOXY-D-PHENYLALANINE
  • N-ALPHA-T-BUTOXYCARBONYL-O-METHYL-D-TYROSINE
CAS:
68856-96-2
MF:
C15H21NO5
MW:
295.33
Product Categories:
  • Unusual Amino Acids
  • Boc-Amino Acids and Derivative
Mol File:
68856-96-2.mol
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BOC-D-TYR(ME)-OH Chemical Properties

Melting point:
93.0 to 97.0 °C
Boiling point:
462.0±40.0 °C(Predicted)
Density 
1.168±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
pka
3.00±0.10(Predicted)
form 
powder to crystal
color 
White to Almost white
optical activity
Consistent with structure
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Safety Information

HazardClass 
IRRITANT
HS Code 
2924297099
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BOC-D-TYR(ME)-OH Usage And Synthesis

Chemical Properties

White powder

Uses

Boc-O-methyl-D-tyrosine is a compound involved in the design and synthesis of β-sheet-based self-assembling cyclic peptides with tunable cavities.

Synthesis

94790-24-6

68856-96-2

General procedure for the synthesis of N-Boc-4-methoxy-D-phenylalanine from methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propionate: in the presence of 1 mL of water, K2CO3 (0.089 g, 0.608 mmol) was added to a (S)-2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl) Methyl propionate (0.100 g, 0.323 mmol) was added to a solution in methanol (4 mL). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, methanol was removed by rotary evaporation. The reaction mixture was diluted with water and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate and petroleum ether (1:1) as eluent to give pure N-Boc-4-methoxy-D-phenylalanine.

References

[1] Tetrahedron Letters, 2012, vol. 53, # 52, p. 7128 - 7130
[2] Journal of Organic Chemistry, 1981, vol. 46, # 9, p. 1944 - 1946
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5607 - 5612

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