N-Boc-D-phenylalaninol

Base Information

• Chemical Name: N-Boc-D-phenylalaninol
• CAS No.: 106454-69-7
• Molecular Formula: C14H21NO3
• Molecular Weight: 251.326
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID10427108
• Nikkaji Number: J756.433C
• Wikidata: Q72450275
• Mol file: 106454-69-7.mol

Synonyms:N-Boc-D-phenylalaninol;106454-69-7;Boc-D-phenylalaninol;(R)-tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate;N-(tert-Butoxycarbonyl)-D-phenylalaninol;(R)-2-(Boc-amino)-3-phenyl-1-propanol;MFCD00216472;tert-butyl N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate;N-Boc- D-phenylalaninol;(R)-N-(tert-Butoxycarbonyl)-beta-phenylalaninol;(R)-2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol;(R)-(+)-2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol;Boc-D-Phe-ol;Boc-D-phenylalaninol, 98%;SCHEMBL257912;DTXSID10427108;tert-butyl (R)-(1-hydroxy-3-phenylpropan-2-yl)carbamate;LDKDMDVMMCXTMO-GFCCVEGCSA-N;AKOS005259794;AKOS015888184;N-tert-butoxycarbonyl-D-Phenylalaninol;CS-W009313;AC-24151;AS-17262;2-(R)-(BOC-amino)-3-pheny-1-propanol;N-(t-butyloxycarbonyl)-(D)-phenylalaninol;2-(R)-(BOC-amino)-3-phenyl-1-propanol;B1966;EN300-73160;A22800;J-800379;Q-101623;(r)-tert-butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate;((R)-1-benzyl-2-hydroxy-ethyl)-carbamic acid t-butyl ester;Boc-D-Phenylalaninol;N-T-BOC-D-PhenylalaninoL;D-(+)-BOC-Phenylalaninol;(R)-2-(Boc-amino)-3-phenyl-1-propanol, N-(tert-Butoxycarbonyl)-D-phenylalaninol

Chemical Property of N-Boc-D-phenylalaninol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.84E-07mmHg at 25°C
• Melting Point: 95-98 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 410.1 °C at 760 mmHg
• PKA: 12.07±0.46(Predicted)
• Flash Point: 201.8 °C
• PSA: 58.56000
• Density: 1.085 g/cm³
• LogP: 2.50560
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 251.15214353
• Heavy Atom Count: 18
• Complexity: 254

Purity/Quality:

98% ^*data from raw suppliers

N-Boc-D-phenylalaninol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1)CO
• Uses: Protected D-Phenylalaninol, an intermediate in the preparation of (S)-Amphetamine.

Technology Process of N-Boc-D-phenylalaninol

There total 48 articles about N-Boc-D-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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-amino-3-phenylpropanol (5267-64-1) → N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7)

Guidance literature:

In dichloromethane; at 0 - 20 ℃;

Reference yield: 100.0%

tert-butyldicarbonate (34619-03-9) + (R)-2-amino-3-phenylpropanol (5267-64-1) → N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 24h;

DOI:10.1021/jm801220a

Reference yield: 90.3%

(R)-4-benzyl-3-t-butoxycarbonyl-2-oxazolidinone (161106-43-0) → N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7)

Guidance literature:

With caesium carbonate; In methanol; for 3h; Ambient temperature;

DOI:10.1246/bcsj.67.3363

upstream raw materials:

methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate

(R)-4-benzyl-3-t-butoxycarbonyl-2-oxazolidinone

di-tert-butyl dicarbonate

(R)-2-amino-3-phenylpropanol

Downstream raw materials:

N-(tert-butoxycarbonyl)-D-phenylalaninal

(2R)-3-phenyl-1-pivaloyloxy-2-propyl amine

t-butyl (1R)-1-benzyl-2-(3-cyanophenoxy)ethylcarbamate

methyl 5-({(2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}oxy)nicotinate

Refernces

• 1、 J?drzejczak, Karol,Hrynczyszyn, Pawe?,Szczesio, Ma?gorzata,Artym, Jolanta,Jastrz?bek, Tomasz,Koci?ba, Maja,G?ówka, Marek,Huben, Krzysztof,Kochanowska, Iwona,Zimecki, Micha?,Zabrocki, Janusz,Jankowski, Stefan,Kolesińska, Beata. "Synthesis and biological activity of cyclolinopeptide A analogues modified with γ4-bis(homo-phenylalanine)". . p. 4265 - 4276. Retrieved 2017.
• 2、 Amira, Aicha,K'Tir, Hacene,Berredjem, Malika,Aouf, Nour-Eddine. "A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-free conditions". . p. 509 - 515. Retrieved 2014.
• 3、 Yao, Lin,Wen, Jialin,Liu, Shaodong,Tan, Renchang,Wood, Noel Marie,Chen, Weiping,Zhang, Shengyong,Zhang, Xumu. "Highly enantioselective hydrogenation of α-oxy functionalized α,β-unsaturated acids catalyzed by a ChenPhos-Rh complex in CF3CH2OH". . p. 2273 - 2276. Retrieved 2016.
• 4、 Debia, Natalí P.,Rodríguez, Juan J.P.,da Silveira, Carolina H.,Chaves, Otavio A.,Iglesias, Bernardo A.,Rodembusch, Fabiano S.,Lüdtke, Diogo S.. "Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution". . . Retrieved 2020/04/27.
• 5、 Reddy Guduru, Shiva Krishna,Chamakuri, Srinivas,Raji, Idris O.,MacKenzie, Kevin R.,Santini, Conrad,Young, Damian W.. "Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production". . p. 11777 - 11793. Retrieved 2018/09/27.