Boc-D-alanine

Base Information

• Chemical Name: Boc-D-alanine
• CAS No.: 7764-95-6
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.211
• Hs Code.: 29241990
• European Community (EC) Number: 616-484-7
• DSSTox Substance ID: DTXSID30348467
• Nikkaji Number: J263.658A
• Wikidata: Q72447739
• Mol file: 7764-95-6.mol

Synonyms:Boc-D-alanine;7764-95-6;Boc-D-Ala-OH;N-Boc-D-alanine;N-(tert-Butoxycarbonyl)-D-alanine;(R)-2-((tert-Butoxycarbonyl)amino)propanoic acid;N-tert-Butoxycarbonyl-D-alanine;N-alpha-t-Boc-D-alanine;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(2R)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;D-ALANINE, N-[(1,1-DIMETHYLETHOXY)CARBONYL]-;(R)-2-(TERT-BUTOXYCARBONYLAMINO)PROPANOIC ACID;MFCD00063123;N-Boc D-Alanine;Boc-(D)-alanine;Boc-(R)-alanine;Boc-DAla-OH;(r)-n-boc-alanine;N-(T-BUTOXYCARBONYL)-D-ALANINE;Boc-(D)Ala-OH;Boc-D -Ala-OH;N-Boc-(D)-Alanine;Boc--D--Ala;(2R)-2-(tert-butoxycarbonylamino)propanoic acid;Boc-(D)-Ala-OH;BOC-D-Ala--OH;BOC-D-ALA;BOC--D--Ala--OH;t-butoxycarbonyl D-alanine;N-t-butoxycarbonyl-D-alanine;N-.alpha.-t-Boc-D-alanine;SCHEMBL256594;(R)-tert-butoxycarbonylalanine;(R)-N-tert-butoxycarbonylalanine;DTXSID30348467;Nalpha-t-butoxycarbonyl-D-alanine;N-(t-butyloxycarbonyl)-D-alanine;N-tertiary-butoxycarbonyl-D-alanine;Nalpha -t-butoxycarbonyl-D-alanine;CS-D1467;HY-Y1164;(R)-N-(tert-butoxycarbonyl)alanine;N-(tert-butyloxycarbonyl)-D-alanine;AR3050;AKOS015922841;(TERT-BUTOXYCARBONYL)-D-ALANINE;(R)-2-(BOC-AMINO)PROPANOIC ACID;AC-24134;AS-12723;Boc-D-Ala-OH, >=98.0% (TLC);BP-12828;(R)-2-tertbutoxycarbonylaminopropionic acid;N-ALPHA-T-BUTYLOXYCARBONYL-D-ALANINE;(R)-2-tert-butoxycarbonylaminopropionic acid;AM20100773;B2175;(R)-2(tert-butoxycarbonylamino)propanoic acid;(R)-2-tert-butoxycarbonylamino-propionic acid;EN300-55380;M03251;N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine;J-300001;Z829930832

Chemical Property of Boc-D-alanine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 6.39E-05mmHg at 25°C
• Melting Point: 81-84 °C
• Refractive Index: 26 ° (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.: Chloroform, 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

Boc-D-Ala ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: 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: N-tert-Boc-D-alanine is an N-Boc-protected form of D-Alanine (A480995). D-Alanine is an amino acid that is commonly found in bacteria, such as Streptococcus faecalis. It is essential for the biosynthesis of peptidoglycan crosslinking sub-units that are used for bacterial cell walls. D-Alanine is also known to cause cytotoxic oxidative stress in brain tumour cells.

Technology Process of Boc-D-alanine

There total 43 articles about Boc-D-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: 85.0%

(R)-benzo[a]acridin-12-ylmethyl 2-(tert-butoxycarbonylamino)propanoate (1609956-66-2) → Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3) + (benzo[a]acridin-12-yl)methanol (1609956-67-3)

Guidance literature:

In water; acetonitrile; for 7.75h; Quantum yield; Photolysis; Inert atmosphere;

DOI:10.1039/c3ob42600a

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:

(6R)-3-benzyl-7t-[(N-tert-butoxycarbonyl-D-alanyl)-amino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

N--N,N'-dicyclohexyl-harnstoff

Tyr-D-Ala-Gly-Phe(αMe)

Tyr-D-Ala-Gly-Phe(αMe)-Leu

Refernces

• 1、 -. "SPIRO-LACTAM COMPOUNDS AND METHODS OF TREATING VIRAL INFECTIONS USING THE SAME". Page/Page column 100; 106. . Retrieved 2021/12/28.
• 2、 de Castro, Pedro P.,Siqueira, Raoni P.,Conforte, Luiza,Franco, Chris H.J.,Bressan, Gustavo C.,Amarante, Giovanni W.. "Cytotoxic activity of synthetic chiral amino acid derivatives". . p. 193 - 200. Retrieved 2019/12/28.