(1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

Base Information

• Chemical Name: (1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one
• CAS No.: 1311174-81-8
• Molecular Formula: C₂₃H₃₈O₆
• Molecular Weight: 410.551
• Mol file: 1311174-81-8.mol

Synonyms:(1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

Chemical Property of (1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

There total 4 articles about (1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-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: 100.0%

(1S,3aS,4R,7aS)-4-{2-[(1S,2S,6S)-1-(iodomethyl)-2-(methoxymethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one (1311174-80-7) → (1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one (1311174-81-8)

Guidance literature:

With zinc; In methanol; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/ol201327u

Reference yield:

C35H66O7Si2 (1311174-78-3) → (1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one (1311174-81-8)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

3: zinc / methanol / 8 h / 20 °C / Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol201327u

Reference yield:

C35H64O7Si2 → (1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-hydroxy-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one (1311174-81-8)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

3: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

4: zinc / methanol / 8 h / 20 °C / Inert atmosphere

With 1H-imidazole; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; iodine; triphenylphosphine; zinc; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol201327u

upstream raw materials:

C₃₅H₆₆O₇Si₂

(1S,3aS,4S,7aS)-4-{2-[(1S,2S,6S)-1-(hydroxymethyl)-2-(methoxymethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

(1S,3aS,4R,7aS)-4-{2-[(1S,2S,6S)-1-(iodomethyl)-2-(methoxymethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]ethyl}-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one

Downstream raw materials:

tert-butyl {(3S,3aS,7S,10aS,12aS,12bR)-3-(methoxymethoxy)-3a-methyl-1,2,3,3a,4,7,8,9,10,11,12,12b-dodecahydro-10a,12a-epoxybenzo[4,5]cyclohepta[1,2-e]inden-7-yl}oxydiphenylsilane

(3S,3aS,5S,6aR,7S,10aS,12bS)-7-[(tert-butyldiphenylsilyl)oxy]-3,10a-bis(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,6a,7,8,9,10,10a,11,12b-tetradecahydrobenzo[4,5]cyclohepta[1,2-e]inden-5-yl acetate

(3S,3aS,5S,7S,10aS,12bS)-7-[(tert-butyldiphenylsilyl)oxy]-3,10a-bis(methoxymethoxy)-3a-methyl-1,2,3,3a,4,5,7,8,9,10,10a,11,12,12b-tetradecahydrobenzo[4,5]cyclohepta[1,2-e]inden-5-yl acetate

(1S,3aS,4R,7aS)-4-{2-[(1S,3S)-3-(tert-butyldiphenylsilyloxy)-1-(methoxymethoxy)-2-methylenecyclohexyl]ethyl}-6-hydroxy-1-(methoxymethoxy)-7a-methylhexahydro-1H-inden-5(6H)-one