CID 12876462

Base Information

• Chemical Name: CID 12876462
• CAS No.: 3845-64-5
• Molecular Formula: C14H22N2O6S
• Molecular Weight: 346.404
• Hs Code.: 29309090
• European Community (EC) Number: 223-341-9
• DSSTox Substance ID: DTXSID901136592
• Nikkaji Number: J217.713G
• Mol file: 3845-64-5.mol

Synonyms:Boc-Met-OSu;N-hydroxysuccinimidyl t-butoxycarbonylmethionine;t-butoxycarbonyl-L-methionine N-hydroxysuccinimidyl ester;t-butoxycarbonylmethionine N-hydroxysuccinimidyl ester;TBM-NHS;tert-butoxycarbonyl-L-methionine N-hydroxysuccinimidyl ester

Chemical Property of CID 12876462

Chemical Property:

• Melting Point: 120-126 °C
• Refractive Index: 1.536
• PSA: 127.31000
• Density: 1.28 g/cm³
• LogP: 1.56880
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 346.11985760
• Heavy Atom Count: 23
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-methionine N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCSC)C(=O)ON1C(=O)CCC1=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCSC)C(=O)ON1C(=O)CCC1=O

Technology Process of CID 12876462

There total 5 articles about CID 12876462 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%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-tert-butoxycarbonyl-L-methionine (2488-15-5) → tertbutoxycarbonyl-L-methionine N-hydroxysuccinimide ester (3845-64-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 18h;

Reference yield: 92.0%

N-tert-butoxycarbonyl-L-methionine (2488-15-5) + 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate (107960-02-1) → tertbutoxycarbonyl-L-methionine N-hydroxysuccinimide ester (3845-64-5)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; acetonitrile; Ambient temperature;

DOI:10.1021/jo00388a005

Reference yield: 35.0%

di(succinimido) carbonate (74124-79-1) + N-tert-butoxycarbonyl-L-methionine (2488-15-5) → tertbutoxycarbonyl-L-methionine N-hydroxysuccinimide ester (3845-64-5)

Guidance literature:

With dmap; In neat (no solvent); for 1h; Milling;

DOI:10.1021/jo500463y

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-tert-butoxycarbonyl-L-methionine

1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate

L-methionine

Downstream raw materials:

Tert-butyloxycarbonylmethionyl-tyrosyl-glycyl-glycyl-phenylalanyl-leucine

N^α-tert-Butyloxycarbonyl-L-methionyl-L-aspartyl-L-phenylalanine amide

2-[2-(2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl ester

[1-(3-{3,5-bis-[3-(2-tert-butoxycarbonylamino-4-methylsulfanyl-butyrylamino)-propyl]-phenyl}-propylcarbamoyl)-3-methylsulfanyl-propyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Koplūnait?, Martyna,Butkut?, Kamil?,Me?kys, Rolandas,Taurait?, Daiva. "Synthesis of pyrimidine nucleoside and amino acid conjugates". supporting information. . Retrieved 2020/11/13.
• 2、 Yang, Jinhua,Wang, Changliu,Xu, Silin,Zhao, Junfeng. "Ynamide-Mediated Thiopeptide Synthesis". supporting information. p. 1382 - 1386. Retrieved 2019/01/08.