methyl (2S)-5-[[(2R)-1-[(2-methoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate

Base Information

• Chemical Name: methyl (2S)-5-[[(2R)-1-[(2-methoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS No.: 120033-58-1
• Molecular Formula: C27H44N6O14S2
• Molecular Weight: 435.499
• DSSTox Substance ID: DTXSID40559042
• Nikkaji Number: J1.749.233K
• Wikidata: Q82441565
• Mol file: 120033-58-1.mol

Synonyms:120033-58-1;N-tert-Butyloxycarbonyl Glutathione Dimethyl Diester;methyl (2S)-5-[[(2R)-1-[(2-methoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate;Methyl (S)-2-(Boc-amino)-5-[[(R)-3-mercapto-1-[(2-methoxy-2-oxoethyl)amino]-1-oxo-2-propyl]amino]-5-oxopentanoate;Methyl N2-(tert-butoxycarbonyl)-N5-((R)-3-mercapto-1-((2-methoxy-2-oxoethyl)amino)-1-oxopropan-2-yl)-L-glutaminate;MFCD28898477;SCHEMBL13138378;DTXSID40559042;methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-{[(1R)-1-[(2-methoxy-2-oxoethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoate;CS-0453843;E79496;J-004245;Dimethyl (4R,9S)-13,13-dimethyl-3,6,11-trioxo-4-(sulfanylmethyl)-12-oxa-2,5,10-triazatetradecane-1,9-dicarboxylate (non-preferred name)

Chemical Property of methyl (2S)-5-[[(2R)-1-[(2-methoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate

Chemical Property:

• PSA: 374.22000
• LogP: 1.86900
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 14
• Exact Mass: 435.16753607
• Heavy Atom Count: 29
• Complexity: 606

Purity/Quality:

99% ^*data from raw suppliers

N-tert-Butyloxycarbonyl glutathione dimethyl diester ^*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(CCC(=O)NC(CS)C(=O)NCC(=O)OC)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)OC)C(=O)OC
• Uses: Protected Glutathione (G597951). The major thiol compound of living plant and animal cells.

Technology Process of methyl (2S)-5-[[(2R)-1-[(2-methoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate

There total 15 articles about methyl (2S)-5-[[(2R)-1-[(2-methoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate 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: 72.0%

bis-(N'-Boc)-L-glutathione disulfide tetramethyl ester (566172-19-8) → methyl N2-(tert-butoxycarbonyl)-N5-((R)-3-mercapto-1-((2-methoxy-2-oxoethyl)amino)-1-oxopropan-2-yl)-L-glutaminate (120033-58-1)

Guidance literature:

With tributylphosphine; In propan-1-ol; water; at 23 ℃; for 4h;

DOI:10.1016/j.bmc.2006.10.022

Reference yield: 70.0%

L-glutathione dimethyl ester hydrochloride + di-tert-butyl dicarbonate (24424-99-5) → 2-tert-butoxycarbonylamino-4-[2-tert-butoxycarbonylsulfanyl-1-(methoxycarbonylmethyl-carbamoyl)-ethylcarbamoyl]-butyric acid methyl ester + methyl N2-(tert-butoxycarbonyl)-N5-((R)-3-mercapto-1-((2-methoxy-2-oxoethyl)amino)-1-oxopropan-2-yl)-L-glutaminate (120033-58-1)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 23 ℃; for 15h;

DOI:10.1016/j.bmc.2006.10.022

Reference yield: 64.0%

N-(tert-butoxycarbonyl)-S-trityl glutathione dimethyl ester (881390-72-3) → methyl N2-(tert-butoxycarbonyl)-N5-((R)-3-mercapto-1-((2-methoxy-2-oxoethyl)amino)-1-oxopropan-2-yl)-L-glutaminate (120033-58-1)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja057521c

upstream raw materials:

N-(tert-butoxycarbonyl)-S-(tert-butylthio)glutathione bis(methyl ester)

N-(tert-butoxycarbonyl)-S-trityl glutathione dimethyl ester

di-tert-butyl dicarbonate

bis-(N'-Boc)-L-glutathione disulfide tetramethyl ester

Downstream raw materials:

S-(N-methylcarbamoyl)glutathione hydrochloride

C₂₉H₄₃N₃O₁₀S

C₅₂H₆₃N₃O₁₄S

C₂₄H₃₄IN₃O₈S

Refernces

• 1、 Chalker, Justin M.,Wood, Charlotte S. C.,Davis, Benjamin G.. "A convenient catalyst for aqueous and protein Suzuki-Miyaura cross-coupling". supporting information; experimental part. p. 16346 - 16347. Retrieved 2010/01/29.
• 2、 Falck,Sangras, Bhavani,Capdevila, Jorge H.. "Preparation of N-tBoc l-glutathione dimethyl and di-tert-butyl esters: Versatile synthetic building blocks". . p. 1062 - 1066. Retrieved 2007/10/03.