Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

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Chemical Name:Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester
CAS No.:793685-05-9
Molecular Formula:C₂₃H₃₂O₄S
Molecular Weight:404.571
Hs Code.:

Synonyms:Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

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Chemical Property of Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

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Technology Process of Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

There total 6 articles about Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester 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: 90.0%

: 1005-56-7
phenylcarbonochloridothioate

: 793685-04-8
(3aR,4S,5R,6aS)-5-Hydroxy-4-((R)-5-methoxy-heptyl)-hexahydro-pentalen-2-one

: 793685-05-9
Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1016/j.tet.2004.06.143

Reference yield:

: 793685-00-4
5-(tert-butyl-dimethyl-silanyloxy)-6-(2-hydroxy-ethyl)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one

: 793685-05-9
Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 90 percent / n-BuLi; AgCl / hexane; tetrahydrofuran / 0.25 h / -78 °C

3.1: H₂; AcOH / Pd/C / 6 h / 2250.23 Torr

3.2: 84 percent / aq. AcOH / 15 h / 50 °C

4.1: 90 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; n-butyllithium; oxalyl dichloride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; silver(I) chloride; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 2.1: Wittig reaction;
DOI:10.1016/j.tet.2004.06.143

Reference yield:

: 793685-01-5
[(1S,2R,6aS)-2-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-4-trimethylsilanyl-1,2,3,5,6,6a-hexahydro-pentalen-1-yl]-acetaldehyde

: 793685-05-9
Thiocarbonic acid O-[(1S,2R,3aS,6aR)-1-((R)-5-methoxy-heptyl)-5-oxo-octahydro-pentalen-2-yl] ester O-phenyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / n-BuLi; AgCl / hexane; tetrahydrofuran / 0.25 h / -78 °C

2.1: H₂; AcOH / Pd/C / 6 h / 2250.23 Torr

2.2: 84 percent / aq. AcOH / 15 h / 50 °C

3.1: 90 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; n-butyllithium; hydrogen; acetic acid; silver(I) chloride; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; 1.1: Wittig reaction;
DOI:10.1016/j.tet.2004.06.143