101555-61-7

Basic information

• Product Name: BOC-D-BETA-HOMOPHENYLALANINE
• Synonyms: BOC-(R)-3-AMINO-4-PHENYLBUTYRIC ACID;BOC-D-BETA-HOPHE-OH;BOC-D-BETA-HOMOPHENYLALANINE;BOC-D-BETA-HOMOPHE-OH;BOC-D-PHE-(C*CH2)OH;(R)-3-BOC-AMINO-4-PHENYLBUTYRIC ACID;(R)-3-TERT-BUTOXYCARBONYLAMINO-4-PHENYL-BUTYRIC ACID;N-BETA-T-BUTOXYCARBONYL-D-BETA-HOMOPHENYLALANINE
• CAS NO: 101555-61-7
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: β-Homo Amino Acids;Beta amino acids;pharmacetical;Amino Acid Derivatives;Pyridines
• Mol File: 101555-61-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 444.837 °C at 760 mmHg
• Flash Point: 222.829 °C
• Appearance: /
• Density: 1.139 g/cm³
• Vapor Pressure: 1.08E-08mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.43±0.10(Predicted)
• CAS DataBase Reference: BOC-D-BETA-HOMOPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-BETA-HOMOPHENYLALANINE(101555-61-7)
• EPA Substance Registry System: BOC-D-BETA-HOMOPHENYLALANINE(101555-61-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• Hazardous Substances Data: 101555-61-7(Hazardous Substances Data)

Usage

Uses

Boc-D-β-homophenylalanine is used in the synthesis of dipeptidyl peptidase IV inhibitors.

InChI:InChI=1/C15H21NO4/c1-15(2,3)20-14(19)16-12(10-13(17)18)9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/t12-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 186581-53-3 diazomethane 
• 18942-49-9 Boc-D-Phe-OH 
• 131270-08-1 (R)-3-amino-4-phenylbutanoic acid 
• 55177-35-0 (E)-4-phenyl-2-butenal 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 300-57-2 allylbenzene 
• 228422-44-4 (R)-1-benzyl-3-hydroxypropylamine 
• 126301-19-7 (2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 106454-69-7 N-tert-butoxycarbonyl-D-Phenylalaninol 
• 145149-49-1 (R)-tert-butyl (1-cyano-3-phenylpropan-2-yl)carbamate 
• 177839-89-3 (R)-tert-butyl 4-hydroxy-1-phenylbutan-2-ylcarbamate 
• 115313-19-4 1-diazo-3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-phenyl-2-butanone 

Downstream Products

• 115364-77-7 (R)-N-tert-butyloxycarbonyl-3-amino-4-phenyl-N'-(benzyloxy)-N'-methylbutanamide 
• 200949-32-2 N-[(2R)-1-carbamoyl-3-phenylpropan-2-yl]carbamic acid tert-butyl ester 
• 193070-97-2 allyl (2S)-2-[3'-N-(tert-Butoxycarbonyl)amino-3'-(R)-benzylpropanoyloxy]-4-methylpentanoate 
• 1236281-13-2 C₂₁H₂₅N₃O₅ 
• 115313-20-7 methyl 3-(R)-[N-(tert-butoxycarbonyl)amino]-4-phenylbutanoate 
• 1271774-40-3 C₁₉H₃₁N₃O₃ 
• 1271777-26-4 C₃₃H₄₈N₄O₇ 
• 1271777-32-2 C₂₃H₃₂N₄O₃ 
• 1271774-26-5 C₁₇H₂₇N₃O₃ 
• 1271774-85-6 C₃₈H₅₈N₄O₈ 
• 1271775-20-2 C₂₄H₃₄N₄O₃ 
• 145149-49-1 (R)-tert-butyl (1-cyano-3-phenylpropan-2-yl)carbamate 

Relevant articles and documents

Concise synthesis of valuable chiral N-Boc-β-benzyl-β-amino acid via construction of chiral N-Boc-3-benzyl-5-oxoisoxazolidine through cross-metathesis/conjugate addition/oxidation

Valuable chiral N-Boc-β-benzyl-β-amino acid was concisely synthesized via construction of chiral N-Boc-3-benzyl-5-oxoisoxazolidine through cross-metathesis/conjugate addition/oxidation. All of the starting materials for the synthesis of chiral N-Boc-β-ben

Synthesis method of chiral N-Boc-3-amino-4-aryl-butyric acid

The invention relates to a synthesis method of chiral N-Boc-3-amino-4-aryl-butyric acid. The method is as below: 1, conducting a cross metathesis reaction, an asymmetric conjugate addition reaction and an oxidation reaction on starting materials including an allyl aromatic compound and crotonaldehyde by a continuous reaction one-pot method to synthesize an N-Boc-3-aryl methyl-5-oxo isoxazole intermediate; or conducting an asymmetric conjugate addition reaction and an oxidation reaction on a starting material (E)-4-aryl-2-crotonaldehyde by a continuous reaction one-pot method to synthesize an N-Boc-3-aryl methyl-5-oxo isoxazole intermediate; and 2, subjecting (3R)-N-Boc-3-aryl methyl-5-oxo isoxazole intermediate by high-pressure hydrogenation to directly prepare the chiral N-Boc-3-amino-4-aryl-butyric acid. The synthesis method provided by the invention has the advantages of simple operation, mild reaction conditions, target product yield reaching 60-69%, and ee value of the target product reaching as high as 96%. The synthetic route has industrialization prospect.

TAPP analogs containing β3-homo-amino acids: Synthesis and receptor binding

β-Amino acids containing α,β-hybrid peptides show great potential as peptidomimetics. In this paper, we describe the synthesis and affinity to μ-opioid and δ-opioid receptors of α,β-hybrids, analogs of the tetrapeptide Tyr- d-Ala-Phe-Phe-NH2 (TAPP). Each amino acid was replaced with an l- or d-β3-h-amino acid. All α,β-hybrids of TAPP analogs were synthesized in solution and tested for affinity to μ-opioid and δ-opioid receptors. The analog Tyr-β3h- d-Ala-Phe-PheNH2 was found to be as active as the native tetrapeptide.