N-Boc-3-Iodo-L-alanine benzyl ester

Base Information

• Chemical Name: N-Boc-3-Iodo-L-alanine benzyl ester
• CAS No.: 108957-20-6
• Molecular Formula: C15H20INO4
• Molecular Weight: 405.233
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID00373549
• Nikkaji Number: J710.711K
• Wikidata: Q72449679
• Mol file: 108957-20-6.mol

Synonyms:108957-20-6;N-Boc-3-Iodo-L-alanine benzyl ester;(R)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate;Boc-beta-iodo-Ala-OBzl;(R)-benzyl 2-(tert-butoxycarbonylamino)-3-iodopropanoate;benzyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;MFCD00191868;Boc- beta -iodo-Ala-OBzl;N-(tert-Butoxycarbonyl)-3-iodo-L-alanine benzyl ester;SCHEMBL1731144;Boc-beta-iodo-Ala-OBzl, 97%;DTXSID00373549;DDXFSYLOWHQCEK-LBPRGKRZSA-N;(r)-2-tert-butoxycarbonylamino-3-iodo-propionic acid benzyl ester;benzyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-iodopropanoate;Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-iodo-, phenylmethyl ester;AKOS016842397;AC-6552;AS-38532;CS-0138067;W-204203;(R)-Benzyl2-((tert-butoxycarbonyl)amino)-3-iodopropanoate;Benzyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate;(R)-2-t-butoxycarbonylamino-3-iodo-propionic acid benzyl ester

Chemical Property of N-Boc-3-Iodo-L-alanine benzyl ester

Chemical Property:

• Vapor Pressure: 1.2E-08mmHg at 25°C
• Melting Point: 78-80 °C(lit.)
• Refractive Index: 1.56
• Boiling Point: 460.1 °C at 760 mmHg
• PKA: 10.42±0.46(Predicted)
• Flash Point: 232 °C
• PSA: 64.63000
• Density: 1.485 g/cm³
• LogP: 3.44900
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 405.04371
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-3-iodo-L-alanineBenzylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CI)C(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CI)C(=O)OCC1=CC=CC=C1
• Uses: N-Boc-3-iodo-L-alanine Benzyl Ester is used as a reactant in the synthesis of the angiotensin-converting enzyme Inhibitors (-)-A58365A and (-)-A58365B lactams.

Technology Process of N-Boc-3-Iodo-L-alanine benzyl ester

There total 10 articles about N-Boc-3-Iodo-L-alanine benzyl 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: 89.0%

N-tert-butoxycarbonyl-L-serine benzyl ester (59524-02-6) → (R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester (108957-20-6)

Guidance literature:

With pyridine; iodine; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b00819

Reference yield: 80.0%

benzyl 2(S)-(tert-butoxycarbonylamino)-3-p-toluenesulfonylpropionate (94882-74-3) → (R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester (108957-20-6)

Guidance literature:

With sodium iodide; In acetone; for 24h; Ambient temperature;

DOI:10.1021/jo00038a030

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester (108957-20-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent

2: 85 percent / pyridine

3: 80 percent / NaI / acetone

With pyridine; sodium iodide; In acetone;

upstream raw materials:

benzyl 2(S)-(tert-butoxycarbonylamino)-3-p-toluenesulfonylpropionate

N-tert-butoxycarbonyl-L-serine benzyl ester

di-tert-butyl dicarbonate

L-serine benzyl ester benzenesulfonate salt

Downstream raw materials:

Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4(R/S)-phenylhex-5-enoate

Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-cyanopropionate

phenylmethyl (S)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hexenoate

benzyl (2-t-butoxycarbonylamino)acrylate

Refernces

• 1、 Koseki, Yohei,Yamada, Haruka,Usuki, Toyonobu. "Efficient synthesis of benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-ω- iodoalkanoates". experimental part. p. 580 - 586. Retrieved 2011/06/21.
• 2、 Stocking, Emily M.,Schwarz, Jessie N.,Senn, Hans,Salzmann, Michael,Silks, Louis A.. "Synthesis of L-selenocystine, L-[77Se]selenocystine and L-tellurocystine". . p. 2443 - 2447. Retrieved 2007/10/03.