Boc-3-iodo-D-alanine methyl ester

Base Information

• Chemical Name: Boc-3-iodo-D-alanine methyl ester
• CAS No.: 170848-34-7
• Molecular Formula: C₉H₁₆INO₄
• Molecular Weight: 329.135
• European Community (EC) Number: 890-205-9
• DSSTox Substance ID: DTXSID30465249
• Nikkaji Number: J3.348.110A
• Wikidata: Q72490917
• Mol file: 170848-34-7.mol

Synonyms:170848-34-7;Boc-3-iodo-D-alanine methyl ester;(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate;Boc-beta-iodo-D-Ala-OMe;(S)-methyl 2-(tert-butoxycarbonylamino)-3-iodopropanoate;MFCD00216580;(S)-2-[(tert-Butoxycarbonyl)amino]-3-iodopropionic acid methyl ester;methyl (2S)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;(S)-METHYL 2-BOC-AMINO-3-IODOPROPIONATE;Methyl (2S)-2-(tert-butoxycarbonylamino)-3-iodo-propanoate;C9H16INO4;Boc-3-iodo-D-Ala-OMe;Boc-?-iodo-Ala-Ome;Boc-A-iodo-D-Ala-OMe;D-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-iodo-, methyl ester;methyl N-(tert-butoxycarbonyl)-3-iodo-D-alaninate;N-(tert-Butoxycarbonyl)-3-iodo-D-alanine methyl ester;SCHEMBL1743738;(S)-Methyl2-((tert-butoxycarbonyl)amino)-3-iodopropanoate;DTXSID30465249;Boc-3-iodo-D-Ala-OMe, 99%;UGZBFCCHLUWCQI-ZCFIWIBFSA-N;CS-Z0021;HY-Z0424;AKOS015899819;AM86005;AC-24326;AC-31646;DS-15270;PD197340;A26605;EN300-199183;N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester;methyl (25)-2-(tert-butoxycarbonylamino)-3-iodo-propanoate;Methyl (2S)-2-[(tert-butoxycarbonyl)-amino]-3-iodopropanoate;methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-iodopropanoate;Methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-3-iodo-D-alaninate;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-IODO-PROPIONIC ACID METHYL ESTER;(R)-methyl 2-(tert-butoxycarbonyl)-3-iodopropanoate

Chemical Property of Boc-3-iodo-D-alanine methyl ester

Chemical Property:

• Vapor Pressure: 2.91E-05mmHg at 25°C
• Melting Point: 55-59oC
• Refractive Index: 1.513
• Boiling Point: 356.475 °C at 760 mmHg
• PKA: 10.44±0.46(Predicted)
• Flash Point: 169.39 °C
• PSA: 64.63000
• Density: 1.552 g/cm³
• LogP: 1.87860
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 329.01241
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-3-iodo-D-alanine methyl ester ^*data from reagent suppliers

Safty Information:

• Statements: 52

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CI)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CI)C(=O)OC
• Uses: (S)-2-[(tert-Butoxycarbonyl)amino]-3-iodopropionic Acid Methyl Ester is a useful reagent for organic synthesis.

Technology Process of Boc-3-iodo-D-alanine methyl ester

There total 14 articles about Boc-3-iodo-D-alanine methyl ester 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: 93.0%

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8) → N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester (170848-34-7,889670-02-4)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/anie.202006260

Reference yield: 85.0%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo901219k

Reference yield: 85.0%

methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate (56926-94-4) → N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4)

Guidance literature:

With sodium iodide; In acetone; for 12h; Heating;

upstream raw materials:

methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate

(S)-2-tert-butoxycarbonylamino-3-methanesulfonyloxypropionic acid methyl ester

N-tert-butyloxycarbonyl-L-serine methyl ester

(S)-N-(tert-butoxycarbonyl)serine

Downstream raw materials:

methyl 2-[(tert-butoxycarbonyl)amino]acrylate

D-N-Boc-nor-leucine methyl ester

methyl (2S)-2-tert-butoxycarbonylaminohexanoate

methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propanoate

Refernces

• 1、 Muller,Schmidt,Jiricek,Hopfgartner,Riehl,Buenzli,Piguetf. "Lanthanide triple helical complexes with a chiral ligand derived from 2,6-pyridinedicarboxylic acid". . p. 2655 - 2662. Retrieved 2001.
• 2、 Danner, Paulami,Morkunas, Marius,Maier, Martin E.. "Synthesis of d -abrines by palladium-catalyzed reaction of ortho-iodoanilines with N -Boc- N -methylalanyl-substituted acetaldehyde and acetylene". . p. 2474 - 2477. Retrieved 2013.
• 3、 Tadd, Andrew C.,Meinander, Kristian,Luthman, Kristina,Wallen, Erik A. A.. "Synthesis of orthogonally protected disulfide bridge mimetics". . p. 673 - 675. Retrieved 2011.
• 4、 -. "ELONGATION FACTOR 1-ALPHA INHIBITORS AND USES THEREOF". Paragraph 0551-0554; 0598-0603. . Retrieved 2021/08/13.
• 5、 -. "MODULATORS OF THE INTEGRATED STRESS RESPONSE PATHWAY". Page/Page column 36; 37; 38. . Retrieved 2020/11/04.