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
• General Description: BOC-D-Alanine, also known as N-tert-Butoxycarbonyl-D-alanine or BOC-D-Ala-OH, is a protected derivative of D-alanine commonly used in peptide synthesis. The BOC (tert-butoxycarbonyl) group serves as a temporary protecting group for the amino functionality, preventing unwanted side reactions during peptide coupling. BOC-D-Alanine is particularly valuable in solid-phase peptide synthesis (SPPS) and other organic synthesis applications where selective deprotection is required. Its chiral nature (D-configuration) makes it useful for incorporating D-amino acids into peptides, which can enhance stability or modify biological activity. The BOC group can be removed under acidic conditions, allowing further functionalization of the amino acid.

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:

Boc-(R)-Ala

N-tert-butoxycarbonyl-L-alanine ethyl ester

N-(tert-Butyloxycarbonyl)-DL-alaninnitril

N-(tert-butyloxycarbonyl)glycine

Refernces

Total syntheses of bacillamide C and neobacillamide A; Revision of their absolute configurations

10.1016/j.tetasy.2013.11.001

The study focuses on the total syntheses of both enantiomers of bacillamide C and neobacillamide A, natural products with bioactivity, and their optical activities. The researchers aimed to resolve the confusion regarding the absolute configurations of these metabolites, which have been derived from microorganisms growing in marine and terrestrial environments. They synthesized the compounds using a stereospecific route from D-(-)-alanine and compared the specific rotation of the synthesized compounds to those reported in literature. The results indicated that the absolute configurations previously proposed for bacillamide C and neobacillamide A should be revised to (S). This finding is significant for genomic studies of their biosynthesis and for the use of bacillamide C as a building block in bioactive cyclic peptides.

Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin a: Application of a gold-catalyzed cyclization

10.1039/c2ob25685a

The research focuses on the total synthesis of piperidine alkaloids, specifically (+)-241D, isosolenopsin, and isosolenopsin A, which are derived from D-alanine. The study employs a gold-catalyzed cyclization as the key step to access the chiral pyridinone intermediates, which are crucial for the synthesis of these alkaloids. The synthesis involves multiple steps, including the preparation of chiral synthons, gold-catalyzed intramolecular cyclization, and stereoselective reductions. The experiments utilized various reactants such as N-Boc-D-alanine, undecyne, BuLi, PPh3AuCl, and AgSbF6, among others, and employed techniques like Arndt–Eistert homologation and catalytic hydrogenation. The synthesized compounds were analyzed using spectroscopic methods (1H and 13C NMR, IR, and HRMS) and optical rotation measurements to confirm their structures and enantiomeric purity.