gamma-Secretase Inhibitor XVI

Base Information

• Chemical Name: gamma-Secretase Inhibitor XVI
• CAS No.: 208255-51-0
• Molecular Formula: C₂₀H₂₀F₂N₂O₄
• Molecular Weight: 390.387
• DSSTox Substance ID: DTXSID90440198
• Wikidata: Q82256449
• ChEMBL ID: CHEMBL4278710
• Mol file: 208255-51-0.mol

Synonyms:gamma-Secretase Inhibitor XVI;208255-51-0;3,5-Difluorophenylacetyl-Ala-Phg-OMe;methyl (2S)-2-[[(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoyl]amino]-2-phenylacetate;Benzeneacetic acid, alpha-[[(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]-1-oxopropyl]amino]-, methyl ester, (alphaS)-;N-[N-3,5-Difluorophenacetyl]-L-alanyl-S-phenylglycine Methyl Ester;gamma -Secretase Inhibitor XVI;CHEMBL4278710;SCHEMBL14886930;DTXSID90440198;J-013655;(S)-methyl 2-((S)-2-(2-(3,5-difluorophenyl)acetamido)propanamido)-2-phenylacetate

Chemical Property of gamma-Secretase Inhibitor XVI

Chemical Property:

• Boiling Point: 601.017 °C at 760 mmHg
• Flash Point: 317.284 °C
• PSA: 84.50000
• Density: 1.272 g/cm³
• LogP: 2.82430
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 390.13911345
• Heavy Atom Count: 28
• Complexity: 544

Purity/Quality:

99%+, ^*data from raw suppliers

γ-SecretaseInhibitorXVI ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)NC(C1=CC=CC=C1)C(=O)OC)NC(=O)CC2=CC(=CC(=C2)F)F
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](C1=CC=CC=C1)C(=O)OC)NC(=O)CC2=CC(=CC(=C2)F)F
• Uses: gamma-Secretase Inhibitor XVI is a γ-secretase inhibitor that selectively blocks Aβ dimer and trimer formation.

Technology Process of gamma-Secretase Inhibitor XVI

There total 5 articles about gamma-Secretase Inhibitor XVI 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:

(S)-Phenylglycine methyl ester (6591-61-3,24461-61-8,26682-99-5,37760-98-8) → N-[N-3,5-difluorophenylacetyl]-1-alanyl-(S)-phenylglycine methyl ester (208255-51-0)

Guidance literature:

Multi-step reaction with 3 steps

1: DCC; HOBt; Et₃N / CH₂Cl₂ / 20 °C

2: H₂ / Pd/C / methanol / 20 °C

3: WSCD*HCl / CH₂Cl₂ / 20 °C

With WSCD*HCl; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.bmcl.2004.01.067

Reference yield:

3,5-difluorophenyl acetic acid (105184-38-1) + (S)-((S)-2-Amino-propionylamino)-phenyl-acetic acid methyl ester → N-[N-3,5-difluorophenylacetyl]-1-alanyl-(S)-phenylglycine methyl ester (208255-51-0)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran;

DOI:10.1016/S0960-894X(02)00684-4

Reference yield:

(S)-2-phenylglycine (2935-35-5) → N-[N-3,5-difluorophenylacetyl]-1-alanyl-(S)-phenylglycine methyl ester (208255-51-0)

Guidance literature:

Multi-step reaction with 4 steps

1: HClO₄ / 20 °C

2: DCC; HOBt; Et₃N / CH₂Cl₂ / 20 °C

3: H₂ / Pd/C / methanol / 20 °C

4: WSCD*HCl / CH₂Cl₂ / 20 °C

With perchloric acid; WSCD*HCl; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.bmcl.2004.01.067

upstream raw materials:

3,5-difluorophenyl acetic acid

(S)-2-phenylglycine

(S)-Phenylglycine methyl ester

(S)-((S)-2-Benzyloxycarbonylamino-propionylamino)-phenyl-acetic acid methyl ester

Refernces

• 1、 Garofalo, Albert W.,Wone, David W.G.,Phuc, Angela,Audia, James E.,Bales, Cheryl A.,Dovey, Harry F.,Dressen, Darren B.,Folmer, Beverly,Goldbach, Erich G.,Guinn, Ashley C.,Latimer, Lee H.,Mabry, Thomas E.,Nissen, Jeffrey S.,Pleiss, Michael A.,Sohn, Stephen,Thorsett, Eugene D.,Tung, Jay S.,Wu, Jing. "A series of C-terminal amino alcohol dipeptide Aβ inhibitors". . p. 3051 - 3053. Retrieved 2007/10/03.