Boc-l-alanine

Base Information

• Chemical Name: Boc-l-alanine
• CAS No.: 15761-38-3
• Deprecated CAS: 186665-28-1,207305-56-4,90580-61-3,911484-43-0
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.211
• Hs Code.: 2924 19 00
• European Community (EC) Number: 239-847-8
• UNII: VBSZA1BT4G
• DSSTox Substance ID: DTXSID40884846
• Nikkaji Number: J208.111C
• Wikidata: Q72509662
• Mol file: 15761-38-3.mol

Synonyms:Boc-Ala;t-BA amino acid;tert-butoxycarbonyl-alanine;tert-butoxycarbonylalanine

Chemical Property of Boc-l-alanine

Chemical Property:

• Appearance/Colour: White to off-white microcrystalline powder
• Vapor Pressure: 6.39E-05mmHg at 25°C
• Melting Point: 79-83 °C(lit.)
• Refractive Index: -25.5 ° (C=2, AcOH)
• Boiling Point: 320.9 °C at 760 mmHg
• PKA: 4.02±0.10(Predicted)
• Flash Point: 147.9 °C
• PSA: 75.63000
• Density: 1.126 g/cm³
• LogP: 1.37510
• Storage Temp.: −20°C
• Solubility.: DMSO, Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 189.10010796
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

N-tert-Boc-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: Boc-Ala-OH can be used: In the preparation of N-propargylalanine, a key precursor to generate N-(3-aryl)propylated alanine residues.In the resolution of racemic mixture of 3,3′-bis(benzyloxy)-1,1′-binaphthalene-2,2′-diol.In the one-pot synthesis of hybrid tripeptidomimetics containing both amide and imide functionalities.

Technology Process of Boc-l-alanine

There total 137 articles about Boc-l-alanine 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%

D-Alanine (338-69-2,25191-17-7,18875-37-1) + di-tert-butyl dicarbonate (24424-99-5) → Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3)

Guidance literature:

D-Alanine; With sodium hydroxide; In water; at 0 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In tetrahydrofuran; water; at 20 ℃;

Reference yield: 84.0%

L-alanin (56-41-7,25191-17-7,18875-37-1) + O-(tert-butyl) S-(pyridin-2-yl)carbonothioate (105678-24-8) → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + L-N-Boc-Ala (15761-38-3)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 75.0%

(R)-2-tertbutoxycarbonylamino-1-propanol (79069-13-9,127516-56-7,147252-84-4,106391-86-0) → Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0040-4039(02)02433-4

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

rac-Ala-OH

tert-butyl alcohol

C₁₁H₁₉NO₆

Downstream raw materials:

t-butoxycarbonyl-L-alanine p-nitroanilide

tert.-Butyloxycarbonyl-L-alanin-o-nitrophenylester

methyl 4,6-O-benzylidene-2,3-di-O-α-D-glucopyranoside

Gly-Pro-Hyp-Gly-Ala-Gly

Refernces

• 1、 Kokan, Zoran,Peri?, Berislav,Vazdar, Mario,Marini?, ?eljko,Viki?-Topi?, Dra?en,Me?trovi?, Ernest,Kirin, Sre?ko I.. "Metal-induced supramolecular chirality inversion of small self-assembled molecules in solution". . p. 1945 - 1948. Retrieved 2017.
• 2、 Golebiowski, Adam,Jacobsson, Ulla,Jurczak, Janusz. "HIGH PRESSURE APPROACH TO THE TOTAL SYNTHESIS OF 6-EPI-D-PURPUROSAMIN B". . p. 3063 - 3066. Retrieved 1987.
• 3、 Mohr, Kathrin I.,Volz, Carsten,Jansen, Rolf,Wray, Victor,Hoffmann, Judith,Bernecker, Steffen,Wink, Joachim,Gerth, Klaus,Stadler, Marc,Müller, Rolf. "Pinensins: The First Antifungal Lantibiotics". . p. 11254 - 11258. Retrieved 2015.
• 4、 Keglevic,D. et al.. "-". . p. 245 - 256. Retrieved 1972.
• 5、 Hamasaki, Keita,Ueno, Akihiko. "Significant enantioselectivity in alanine ester hydrolysis catalyzed by imidazole attached β-cyclodextrins". . p. 859 - 860. Retrieved 1995.
• 6、 Blake,Li. "Adrenocorticotropin. 48. Synthesis and biological activity of [15,16 D lysine, 17,18 D arginine] adrenocorticotropin (1 19) and an all D retropeptide related to the amino terminal octadecapeptide of adrenocorticotropin". . p. 589 - 595. Retrieved 1976.
• 7、 Garnier-Amblard, Ethel C.,Mays, Suzanne G.,Arrendale, Richard F.,Baillie, Mark T.,Bushnev, Anatoliy S.,Culver, Deborah G.,Evers, Taylor J.,Holt, Jason J.,Howard, Randy B.,Liebeskind, Lanny S.,Menaldino, David S.,Natchus, Michael G.,Petros, John A.,Ramaraju, Harsha,Reddy, G. Prabhakar,Liotta, Dennis C.. "Novel synthesis and biological evaluation of enigmols as therapeutic agents for treating prostate cancer". . p. 438 - 443. Retrieved 2011.
• 8、 -. "SPIRO-LACTAM COMPOUNDS AND METHODS OF TREATING VIRAL INFECTIONS USING THE SAME". Page/Page column 100; 106. . Retrieved 2021/12/28.
• 9、 Mandal, Raki,Mahanty, Kingshuk,Mandal, Subhendu,De Sarkar, Suman,Tarafdar, Pradip K.. "Membrane transport inspired hydrolysis of non-activated esters at near physiological pH". supporting information. p. 11088 - 11091. Retrieved 2021/10/30.