ALOC-D-PHE-OH DCHA

Base Information

• Chemical Name: ALOC-D-PHE-OH DCHA
• CAS No.: 152507-71-6
• Molecular Formula: C13H15 N O4
• Molecular Weight: 249.266
• Mol file: 152507-71-6.mol

Synonyms:D-Phenylalanine,N-[(2-propenyloxy)carbonyl]- (9CI)

Chemical Property of ALOC-D-PHE-OH DCHA

Chemical Property:

• Boiling Point: 428.4±45.0 °C(Predicted)
• PKA: 3.84±0.10(Predicted)
• PSA: 87.66000
• Density: 1.203±0.06 g/cm3(Predicted)
• LogP: 5.61770
• Storage Temp.: -15°C

Purity/Quality:

98%min ^*data from raw suppliers

Allyloxycarbonyl-D-phenylalaninedicyclohexylammoniumsalt,99%(HPLC) 99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ALOC-D-PHE-OH DCHA

There total 5 articles about ALOC-D-PHE-OH DCHA which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) + Allyl chloroformate (2937-50-0) → (R)-(N-allyloxycarbonyl)phenylalanine (152507-71-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00810

Reference yield:

4-benzyl-2,5-dioxo-oxazolidine-3-carboxylic acid allyl ester (394210-47-0) → N-allyloxycarbonyl-(S)-phenylalanate (90508-20-6) + (R)-(N-allyloxycarbonyl)phenylalanine (152507-71-6)

Guidance literature:

4-benzyl-2,5-dioxo-oxazolidine-3-carboxylic acid allyl ester; With methanol; 4 A molecular sieve; In diethyl ether; at -60 ℃; for 15h;

With water; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja011936q

Reference yield:

Phenylalanine (150-30-1,25191-15-5,658-69-5,67675-33-6) → (R)-(N-allyloxycarbonyl)phenylalanine (152507-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 50 °C

2.1: NMM / tetrahydrofuran / -25 - 20 °C

3.1: 10 mol percent (DHQD)2AQN; 4 Angstroem molecular sieves; methanol / diethyl ether / 15 h / -60 °C

3.2: H₂O

With 4-methyl-morpholine; methanol; 4 A molecular sieve; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja011936q

upstream raw materials:

D-(R)-phenylalanine

diallyl dicarbonate

4-benzyl-2,5-dioxo-oxazolidine-3-carboxylic acid allyl ester

Phenylalanine

Downstream raw materials:

Carbonic acid 4-{(S)-6-allyloxycarbonylamino-2-[(S)-2-((R)-2-allyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-hexanoylamino}-benzyl ester 4-nitro-phenyl ester

[(S)-5-[(S)-2-((R)-2-Allyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-5-(4-hydroxymethyl-phenylcarbamoyl)-pentyl]-carbamic acid allyl ester

(S)-6-Allyloxycarbonylamino-2-[(S)-2-((R)-2-allyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-hexanoic acid

Refernces

• 1、 -. "CHROMOGENIC AND FLUOROGENIC PEPTIDE SUBSTRATES FOR THE DETECTION OF SERINE PROTEASE ACTIVITY". Page/Page column 17; 23; 24. . Retrieved 2017/02/28.
• 2、 Hang,Tian,Tang,Deng. "Asymmetric synthesis of α-amino acids via cinchona alkaloid-catalyzed kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides". . p. 12696 - 12697. Retrieved 2007/10/03.