Z-L-Phenylalaninol

Base Information

• Chemical Name: Z-L-Phenylalaninol
• CAS No.: 6372-14-1
• Molecular Formula: C17H19NO3
• Molecular Weight: 285.343
• Hs Code.: 29051990
• DSSTox Substance ID: DTXSID70357437
• Nikkaji Number: J566.162E
• Wikidata: Q72516358
• Metabolomics Workbench ID: 114391
• ChEMBL ID: CHEMBL164485
• Mol file: 6372-14-1.mol

Synonyms:Cbz-phenylalaninol;N-(carbobenzoxy)phenylalaninol;N-benzoxycarbonyl-phenylalaninol;N-benzyloxycarbonylphenylalaninol;N-carbobenzyloxyphenylalaninol

Chemical Property of Z-L-Phenylalaninol

Chemical Property:

• Vapor Pressure: 2.23E-10mmHg at 25°C
• Melting Point: 92-95 °C
• Refractive Index: -42 ° (C=2, MeOH)
• Boiling Point: 489 °C at 760 mmHg
• PKA: 11.86±0.46(Predicted)
• Flash Point: 249.6 °C
• PSA: 58.56000
• Density: 1.175 g/cm³
• LogP: 2.90730
• Storage Temp.: Store at 0-5°C
• Water Solubility.: insoluble
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 285.13649347
• Heavy Atom Count: 21
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

N-Benzyloxycarbonyl-L-phenylalaninol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CO)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](CO)NC(=O)OCC2=CC=CC=C2
• Uses: Employed in the synthesis of biochemically active compounds. Building block for the synthesis of HIV protease inhibitors.

Technology Process of Z-L-Phenylalaninol

There total 51 articles about Z-L-Phenylalaninol 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: 98.0%

L-Phenylalaninol (3182-95-4) + benzyl chloroformate (501-53-1,94274-21-2) → N-((benzyloxy)carbonyl)-L-phenylalaninol (6372-14-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1007/s11426-012-4607-9

Reference yield: 98.0%

[1-(tert-butyldimethylsilanyloxymethyl)-2-phenylethyl]carbamic acid benzyl ester → N-((benzyloxy)carbonyl)-L-phenylalaninol (6372-14-1)

Guidance literature:

With phosphomolybdic acid hydrate; silica gel; In tetrahydrofuran; at 20 ℃; for 0.333333h;

DOI:10.1021/jo0502697

Reference yield: 96.0%

N-Cbz-L-Phe (1161-13-3) → N-((benzyloxy)carbonyl)-L-phenylalaninol (6372-14-1)

Guidance literature:

N-Cbz-L-Phe; With 4-methyl-morpholine; isobutyl chloroformate; In 1,2-dimethoxyethane; at -15 ℃;

With sodium tetrahydroborate; In 1,2-dimethoxyethane; water; at 15 ℃;

DOI:10.3390/ijms22179447

upstream raw materials:

Benzyl N-hydroxycarbamate

allylbenzene

benzyloxycarbonylamino-4-chlorobenzoate

benzyl chloroformate

Downstream raw materials:

Z-PheΨ(CH2O)GLy-OCH3

benzyl (1S)-(1-formyl-2-phenylethyl)carbamate

C₂₁H₂₃NO₆

C₂₁H₂₇NO₃

Refernces

• 1、 Soley, Jacob,Taylor, Scott D.. "Mild, Rapid, and Chemoselective Procedure for the Introduction of the 9-Phenyl-9-fluorenyl Protecting Group into Amines, Acids, Alcohols, Sulfonamides, Amides, and Thiols". . . Retrieved 2020/02/04.
• 2、 Santhosh,Durgamma,Shekharappa,Sureshbabu, Vommina V.. "Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates". . p. 4874 - 4880. Retrieved 2018/07/15.