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

Base Information

Chemical Name:(3aR,4S,5R,6aS)-5-Hydroxy-4-((R)-5-methoxy-heptyl)-hexahydro-pentalen-2-one
CAS No.:793685-04-8
Molecular Formula:C₁₆H₂₈O₃
Molecular Weight:268.397
Hs Code.:

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

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Chemical Property of (3aR,4S,5R,6aS)-5-Hydroxy-4-((R)-5-methoxy-heptyl)-hexahydro-pentalen-2-one

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Technology Process of (3aR,4S,5R,6aS)-5-Hydroxy-4-((R)-5-methoxy-heptyl)-hexahydro-pentalen-2-one

There total 5 articles about (3aR,4S,5R,6aS)-5-Hydroxy-4-((R)-5-methoxy-heptyl)-hexahydro-pentalen-2-one 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: 84.0%

: 793685-03-7
(5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-(R)-5-methoxy-hept-2-enyl)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one

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

Guidance literature:: (5R,6S,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-(R)-5-methoxy-hept-2-enyl)-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one; With hydrogen; acetic acid; palladium on activated charcoal; for 6h; under 2250.23 Torr;

With acetic acid; at 50 ℃; for 15h; Further stages.;
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

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

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; hydrogen; acetic acid; silver(I) chloride; palladium on activated charcoal; In tetrahydrofuran; hexane; 1.1: Wittig reaction;
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

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

Guidance literature:: Multi-step reaction with 3 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

With 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