kynostatin

Base Information

• Chemical Name: kynostatin
• CAS No.: 147384-69-8
• Molecular Formula: C₃₅H₄₅N₅O₆S₂
• Molecular Weight: 695.904
• Mol file: 147384-69-8.mol

Synonyms:4-Thiazolidinecarboxamide,N-(1,1-dimethylethyl)-3-[(2S,3S)-2-hydroxy-3-[[(2R)-2-[[(5-isoquinolinyloxy)acetyl]amino]-3-(methylthio)-1-oxopropyl]amino]-1-oxo-4-phenylbutyl]-5,5-dimethyl-,(4R)- (9CI); 4-Thiazolidinecarboxamide,N-(1,1-dimethylethyl)-3-[2-hydroxy-3-[[2-[[(5-isoquinolinyloxy)acetyl]amino]-3-(methylthio)-1-oxopropyl]amino]-1-oxo-4-phenylbutyl]-5,5-dimethyl-,[4R-[3[2S*,3S*(R*)],4R*]]-; KNI 2227; KNI 227; Kynostatin 227

Chemical Property of kynostatin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1030.4°Cat760mmHg
• PKA: 12.44±0.46(Predicted)
• Flash Point: 577°C
• PSA: 211.03000
• Density: 1.261g/cm³
• LogP: 5.60340

Purity/Quality:

98%Min ^*data from raw suppliers

KYNOSTATIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of kynostatin

There total 10 articles about kynostatin 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:

(R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (158941-58-3) → Kynostatin-227 (147384-69-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1-hydroxybenzotriazol; N,N'-dicyclohexylcarbodiimide / ethyl acetate

2: HCl / dioxane; CH₂Cl₂ / 2 h

3: 90 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

4: HCl / dioxane; CH₂Cl₂ / 2 h

5: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl; TEA / dimethylformamide

With hydrogenchloride; TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1310

Reference yield:

(R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (117918-23-7) → Kynostatin-227 (147384-69-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: TEA; diphenylphosphoryl chloride / ethyl acetate / 1 h

1.2: ethyl acetate

2.1: HCl / dioxane; CH₂Cl₂ / 2 h

3.1: 1-hydroxybenzotriazol; N,N'-dicyclohexylcarbodiimide / ethyl acetate

4.1: HCl / dioxane; CH₂Cl₂ / 2 h

5.1: 90 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

6.1: HCl / dioxane; CH₂Cl₂ / 2 h

7.1: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl; TEA / dimethylformamide

With hydrogenchloride; TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; Diphenylphosphinic chloride; In 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1310

Reference yield:

(R)-4-tert-Butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester (148983-13-5) → Kynostatin-227 (147384-69-8)

Guidance literature:

Multi-step reaction with 6 steps

1: HCl / dioxane; CH₂Cl₂ / 2 h

2: 1-hydroxybenzotriazol; N,N'-dicyclohexylcarbodiimide / ethyl acetate

3: HCl / dioxane; CH₂Cl₂ / 2 h

4: 90 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

5: HCl / dioxane; CH₂Cl₂ / 2 h

6: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl; TEA / dimethylformamide

With hydrogenchloride; TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1310

upstream raw materials:

5-isoquinolinyloxyacetic acid

(R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

(R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

(R)-4-tert-Butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Refernces

• 1、 Mimoto, Tsutomu,Hattori, Naoko,Takaku, Haruo,Kisanuki, Sumitsugu,Fukazawa, Tominaga,Terashima, Keisuke,Kato, Ryohei,Nojima, Satoshi,Misawa, Satoru,Ueno, Takamasa,Imai, Junya,Enomoto, Hiroshi,Tanaka, Shigeki,Sakikawa, Hiroshi,Shintani, Makoto,Hayashi, Hideya,Kiso, Yoshiaki. "Structure-activity relationship of orally potent tripeptide-based HIV protease inhibitors containing hydroxymethylcarbonyl isostere". . p. 1310 - 1326. Retrieved 2007/10/03.