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Boc-D-Phenylglycine

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  • Boc-D-Phg-OH
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  • 2026-05-19
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  • Boc-D-Phenylglycine
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  • $0.00 / 1kg
  • 2025-04-04
  • CAS:33125-05-2
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Boc-D-Phenylglycine Basic information
Product Name:Boc-D-Phenylglycine
Synonyms:Boc-(R)-2-aminobenzeneacetic acid;N-(tert-Butoxycarbonyl)-D-2-phenylglycine;N-Boc-D-2-phenylglycine;N-(tert-butoxycarbonyl)-D-alpha-phenylglycine;N-Boc-D-2-phenylglycine Boc-D-Phg-OH;(R)-2-((tert-butoxycarbonyl)aMino)-2-phenylacetic acid;N-Boc-D-phenylglycine (Boc-D-Phg-OH);BOC-(PHENYL)GLY-OH
CAS:33125-05-2
MF:C13H17NO4
MW:251.28
EINECS:1533716-785-6
Product Categories:Phenylglycine [Phg];Unusual Amino Acids;Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
Mol File:33125-05-2.mol
Boc-D-Phenylglycine Structure
Boc-D-Phenylglycine Chemical Properties
Melting point 88-91 °C
alpha -142 º (c=1% in ethanol)
Boiling point 407.2±38.0 °C(Predicted)
density 1.182±0.06 g/cm3(Predicted)
refractive index -140 ° (C=1, EtOH)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO, Methanol
pka3.51±0.10(Predicted)
form Crystalline Powder
color White
Optical Rotation[α]20/D 141.0±5.0°, c = 1% in ethanol
Water Solubility Insoluble in water. Slightly soluble in DMSO and methanol.
BRN 3033982
Major Applicationpeptide synthesis
InChIInChI=1S/C13H17NO4/c1-13(2,3)18-12(17)14(9-11(15)16)10-7-5-4-6-8-10/h4-8H,9H2,1-3H3,(H,15,16)
InChIKeyKIAPYAZGXJCKQL-UHFFFAOYSA-N
SMILESC(O)(=O)CN(C(OC(C)(C)C)=O)C1=CC=CC=C1
CAS DataBase Reference33125-05-2(CAS DataBase Reference)
Safety Information
Safety Statements 24/25
WGK Germany 3
HazardClass IRRITANT
HS Code 29242990
Storage Class13 - Non Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Boc-D-Phenylglycine Usage And Synthesis
Chemical PropertiesWhite powder
UsesIt is a reagent of choice for assignment of absolute configuration of chiral primary amines by 1H NMR, giving better results than Mosher's acid ((R)-(+)--Methoxy--(trifluoromethyl)-phenyl-acetic acid. αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is D-(+)-2-Phenylglycine with Boc protecting group. (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is used as part of a catalyst combination to catalyze regioselective [4 + 2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. It can also be used to catalyze stereoselective preparation of polyfunctional nitrocyclohexene carboxaldehydes.
reaction suitabilityreaction type: Boc solid-phase peptide synthesis
Synthesis
Di-tert-butyl dicarbonate

24424-99-5

D-2-Phenylglycine

875-74-1

Boc-D-Phenylglycine

33125-05-2

(1) A mixture of (R)-2-amino-2-phenylacetic acid (200 g, 1.32 mol) and potassium carbonate (218 g, 1.58 mol) was dissolved in a solvent mixture of water (2.0 L) and methanol (0.5 L), and cooled to a temperature of less than 10°C. Di-tert-butyl dicarbonate (288 g, 1.32 mol) was added dropwise, and the reaction was stirred at room temperature after the addition. After the addition, the reaction was stirred at room temperature overnight. After completion of the reaction, the pH of the reaction solution was adjusted to 4-5 with 1 N hydrochloric acid, followed by extraction with ethyl acetate (1.0 L × 3). The organic phases were combined, washed with saturated saline (1.0 L × 1), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a white solid product (315 g) in 95% yield.

References[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 968 - 978
[3] Tetrahedron Letters, 1995, vol. 36, # 29, p. 5227 - 5230
[4] Patent: CN104592163, 2016, B. Location in patent: Paragraph 0041; 0042
[5] Patent: CN106748892, 2017, A. Location in patent: Paragraph 0051; 0053; 0054; 0055
Boc-D-Phenylglycine Preparation Products And Raw materials
Raw materialsDi-tert-butyl dicarbonate-->D-2-Phenylglycine-->Water-->Potassium carbonate-->Methanol
Tag:Boc-D-Phenylglycine(33125-05-2) Related Product Information
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