O-Benzyl-L-isoleucine toluene-p-sulphonate

Base Information

• Chemical Name: O-Benzyl-L-isoleucine toluene-p-sulphonate
• CAS No.: 16652-75-8
• Molecular Formula: C13H19NO2^.C7H8O3S
• Molecular Weight: 393.504
• Hs Code.: 2923900090
• European Community (EC) Number: 240-701-0
• DSSTox Substance ID: DTXSID50937211
• Mol file: 16652-75-8.mol

Synonyms:16652-75-8;H-Ile-Obzl Tos;L-isoleucine benzyl ester tosylate;O-Benzyl-L-isoleucine toluene-p-sulphonate;(2S,3S)-Benzyl 2-amino-3-methylpentanoate 4-methylbenzenesulfonate;Benzyl (2s,3s)-2-amino-3-methylpentanoate;4-methylbenzenesulfonic acid;L-Isoleucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1);H-L-Ile-OBzl*Tos;EINECS 240-701-0;L-Ile-OBzl.TosOH;H-Ile-OBzl.Tos-OH;SCHEMBL1287363;Isoleucine benzyl ester tosylate;DTXSID50937211;XAWVXTVKSVYPNE-JGAZGGJJSA-N;MFCD00050511;AKOS015842533;AKOS015909594;AM81853;FD21802;Benzyl L-isoleucinate p-toluenesulfonate;AS-49207;CS-0129849;Benzyl L-isoleucinate 4-methylbenzenesulfonate;A810744;4-Methylbenzene-1-sulfonic acid--benzyl isoleucinate (1/1);(2S,3S)-Benzyl2-amino-3-methylpentanoate4-methylbenzenesulfonate;benzyl (2S,3S)-2-amino-3-methyl-pentanoate

Chemical Property of O-Benzyl-L-isoleucine toluene-p-sulphonate

Chemical Property:

• Vapor Pressure: 1.03E-12mmHg at 25°C
• Melting Point: 153-155 °C
• Boiling Point: 545.1 °C at 760 mmHg
• Flash Point: 283.4 °C
• PSA: 115.07000
• LogP: 5.12600
• Storage Temp.: Store at RT.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 393.16099414
• Heavy Atom Count: 27
• Complexity: 418

Purity/Quality:

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

L-Isoleucine benzyl ester 4-toluenesulfonate salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)OCC1=CC=CC=C1)N.CC1=CC=C(C=C1)S(=O)(=O)O
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)OCC1=CC=CC=C1)N.CC1=CC=C(C=C1)S(=O)(=O)O
• Uses: L-?Isoleucine Benzyl Ester 4-Toluenesulfonate Salt is a reagent used in the preparation of novel 10-hydroxycamptothecin prodrugs used in antitumor treatment. Also used in the synthesis of proteasome inhibitors, cystargolides A & B.

Technology Process of O-Benzyl-L-isoleucine toluene-p-sulphonate

There total 2 articles about O-Benzyl-L-isoleucine toluene-p-sulphonate 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: 91.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6,185532-71-2) → L-isoleucine benzyl ester tosylate (16652-75-8)

Guidance literature:

In benzene; at 70 - 115 ℃; for 8h; Dean-Stark;

DOI:10.1021/acs.jnatprod.7b00383

Reference yield:

L-isoleucine benzyl ester (42406-72-4) + toluene-4-sulfonic acid (104-15-4) → L-isoleucine benzyl ester tosylate (16652-75-8)

Guidance literature:

In diethyl ether;

DOI:10.2174/157017810790533940

Reference yield: 100.0%

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) + L-isoleucine benzyl ester tosylate (16652-75-8) → (2S,3S)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-3-methyl-pentanoic acid benzyl ester

Guidance literature:

(S)-N-(tert-butoxycarbonyl)serine; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

L-isoleucine benzyl ester tosylate; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1039/b211644h

upstream raw materials:

L-isoleucine

toluene-4-sulfonic acid

benzyl alcohol

L-isoleucine benzyl ester

Downstream raw materials:

N-(tert-Butyloxycarbonyl)glycyl-L-isoleucin-benzylester

Boc-Ile₂-OBzl

Nα-diethylphosphinoylisoleucine benzyl ester

(2S,3S)-2-(tert-Butoxycarbonylmethyl-amino)-3-methyl-pentanoic acid benzyl ester; compound with toluene-4-sulfonic acid

Refernces

• 1、 Biondini, Daniele,Brinchi, Lucia,Germani, Raimondo,Goracci, Laura,Savelli, Gianfranco. "Esterification of unprotected a-Amino acids in ionic liquids as the reaction media". experimental part. p. 39 - 44. Retrieved 2010/08/22.
• 2、 Damm, Wolfgang,Hoffmann, Ursula,Macko, Ludwig,Neuburger, Markus,Zehnder, Margareta,Giese, Bernd. "Stereoselective Reactions of α-Imide Substituted Radicals". . p. 7029 - 7048. Retrieved 2007/10/02.