5-tert-butyl-4-({6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-(1-methylethyl)-4-oxo-3,4-dihydro-2H-pyran-5-yl}sulfanyl)-2-methylphenyl ethylsulfamate

Base Information

• Chemical Name: 5-tert-butyl-4-({6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-(1-methylethyl)-4-oxo-3,4-dihydro-2H-pyran-5-yl}sulfanyl)-2-methylphenyl ethylsulfamate
• CAS No.: 207736-26-3
• Molecular Formula: C29H39NO7S2
• Molecular Weight: 577.7525
• Mol file: 207736-26-3.mol

Synonyms:Dihydropyran-2-one deriv. 65;

Chemical Property of 5-tert-butyl-4-({6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-(1-methylethyl)-4-oxo-3,4-dihydro-2H-pyran-5-yl}sulfanyl)-2-methylphenyl ethylsulfamate

Chemical Property:

• Vapor Pressure: 1.39E-18mmHg at 25°C
• Boiling Point: 664.9°C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 355.9°C
• PSA: 155.84000
• Density: 1.3g/cm³
• LogP: 7.53910

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-tert-butyl-4-({6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-(1-methylethyl)-4-oxo-3,4-dihydro-2H-pyran-5-yl}sulfanyl)-2-methylphenyl ethylsulfamate

There total 8 articles about 5-tert-butyl-4-({6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-(1-methylethyl)-4-oxo-3,4-dihydro-2H-pyran-5-yl}sulfanyl)-2-methylphenyl ethylsulfamate 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: 59.0%

4-hydroxy-6-[2-(4-hydroxy-phenyl)ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (207736-87-6) + toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) ester (207737-21-1) → ethyl-sulfamic acid 5-tert-butyl-4-{4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester (207736-26-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm990281p

Reference yield:

4-tert-butyl-2-nitrotoluene (62559-08-4) → ethyl-sulfamic acid 5-tert-butyl-4-{4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester (207736-26-3)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Raney Ni / methanol / 15 h / 35 °C / 2689.24 Torr

2: aq. NaNO₂; aq. 15percent H₂SO₄ / 0.5 h / 70 °C

3: Br₂; NaBr / methanol / 0.5 h / 5 - 40 °C

4: 79 percent / dithiothreitol; 0.02M KH₂PO₄ / ethanol / 4 h / Heating

5: 91 percent / pyridine / CCl₄

6: 98 percent / Et₃N / diethyl ether / 0.5 h

7: 59 percent / K₂CO₃ / dimethylformamide / 20 °C

With pyridine; potassium dihydrogenphosphate; hydrogen; bromine; potassium carbonate; triethylamine; sodium bromide; sodium nitrite; diothiothreitol; nickel; In methanol; tetrachloromethane; diethyl ether; ethanol; N,N-dimethyl-formamide; 1: Reduction / 2: Diazotization / 3: Substitution / 4: Hydrolysis / 5: Tosylation / 6: Sulfonylation / 7: Substitution;

DOI:10.1021/jm990281p

Reference yield:

5-(tert-butyl)-2-methylphenol (5781-02-2) → ethyl-sulfamic acid 5-tert-butyl-4-{4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester (207736-26-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Br₂; NaBr / methanol / 0.5 h / 5 - 40 °C

2: 79 percent / dithiothreitol; 0.02M KH₂PO₄ / ethanol / 4 h / Heating

3: 91 percent / pyridine / CCl₄

4: 98 percent / Et₃N / diethyl ether / 0.5 h

5: 59 percent / K₂CO₃ / dimethylformamide / 20 °C

With pyridine; potassium dihydrogenphosphate; bromine; potassium carbonate; triethylamine; sodium bromide; diothiothreitol; In methanol; tetrachloromethane; diethyl ether; ethanol; N,N-dimethyl-formamide; 1: Substitution / 2: Hydrolysis / 3: Tosylation / 4: Sulfonylation / 5: Substitution;

DOI:10.1021/jm990281p

upstream raw materials:

4-hydroxy-6-[2-(4-hydroxy-phenyl)ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) ester

5-(tert-butyl)-2-methylphenol

4-tert-butyl-2-nitrotoluene

Refernces

• 1、 Vara Prasad,Markoski, Larry J.,Boyer, Fred E.,Domagala, John M.,Ellsworth, Edmund L.,Gajda, Christopher,Hagen, Susan E.,Tait, Bradley D.,Lunney, Elizabeth A.,Tummino, Peter J.,Ferguson, Donna,Holler, Tod,Hupe, Donald,Nouhan, Carolyn,Gracheck, Stephen J.,VanderRoest, Steven,Saunders, James,Iyer,Sinz. "Nonpeptidic HIV protease inhibitors: 6-alkyl-5,6-dihydropyran-2ones possessing a novel and achiral 3-(2-t-butyl-5-methyl-4-sulfamate)phenylthio moiety". . p. 2217 - 2222. Retrieved 2007/10/03.