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Boc-D-Ser(Bzl)-OH

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Boc-D-Ser(Bzl)-OH Basic information

Product Name:
Boc-D-Ser(Bzl)-OH
Synonyms:
  • (2R)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propanoic acid
  • (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(phenylmethoxy)propanoic acid
  • (2R)-2-[(tert-butoxy-oxomethyl)amino]-3-(phenylmethoxy)propanoic acid
  • (2R)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propionic acid
  • L-Serine, N-((1,1-dimethylethoxy)carbonyl)-O-(phenylmethyl)-
  • Boc-D-Ser(Bzl)-OH, >=98%
  • BOC-D-SERINE(BZL)-OH
  • BOC-D-SER(BZL)-OH
CAS:
47173-80-8
MF:
C15H21NO5
MW:
295.33
EINECS:
827-299-8
Product Categories:
  • Boc-Amino Acids and Derivative
  • Amino Acids (N-Protected)
  • Amino Acids
  • Biochemistry
  • Boc-Amino Acids
  • Boc-Amino acid series
Mol File:
47173-80-8.mol
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Boc-D-Ser(Bzl)-OH Chemical Properties

Melting point:
58-60 °C(lit.)
alpha 
-19 º (c=2 80% alcohol)
Boiling point:
437.02°C (rough estimate)
Density 
1.1454 (rough estimate)
refractive index 
-20 ° (C=2, 80% EtOH)
storage temp. 
Sealed in dry,Room Temperature
solubility 
almost transparency in Methanol
pka
3.53±0.10(Predicted)
form 
Powder
color 
White
BRN 
2665080
InChI
InChI=1S/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)10-20-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/t12-/m1/s1
InChIKey
DMBKPDOAQVGTST-GFCCVEGCSA-N
SMILES
C(O)(=O)[C@@H](COCC1=CC=CC=C1)NC(OC(C)(C)C)=O
CAS DataBase Reference
47173-80-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
24/25-36-26
WGK Germany 
3
HS Code 
2924 29 70
HazardClass 
IRRITANT

MSDS

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Boc-D-Ser(Bzl)-OH Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

N-BOC-O-Benzyl-D-serine, is an amino acid derivative used in chemical synthesis and peptide chemistry.is used in preparation of substituted naphthyl thiadiazolidinones as protein tyrosine phosphatase degraders for treating cancer and metabolic diseases.

Biological Activity

Boc-O-benzyl-D-serine is an inhibitor of the uptake of galactose and its derivatives. It has potent inhibitory activity against the uptake of galactose, glucose, and lactose. This drug is also effective in inhibiting the uptake of tetrazole, a substance that inhibits glycolysis. Boc-O-benzyl-D-serine is able to inhibit atherosclerotic lesions caused by piperidine, which has been shown to be synthesized from benzyl alcohol and piperidine. The oral administration of this compound can enhance fibroblast cells that are resistant to insulin.

Synthesis

N-Boc D-Se (500 mg, 2.43 mmol) dissolved in anhydrous DMF (4 mL) was slowly added to a dispersion of 60% NaH (204 mg, 5.1 mmol) in anhydrous DMF at 0 ° C. Stir the mixture at room temperature for 1 hour and cool to 0 ° C. Subsequently, benzyl bromide (0.29 mL, 2.43 mmol) was added and the mixture was heated to room temperature. After 4 hours of reaction, add saturated NH4Cl (1 mL) to quench the reaction. Finally, the product Boc-D-Ser(Bzl)-OH was obtained through purification.

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