Ethanone, 1-[(1S,2R,3R,4S)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-[[(4-methoxy phenyl)methoxy]methyl]-3-methylcyclopentyl]-

Base Information

• Chemical Name: Ethanone, 1-[(1S,2R,3R,4S)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-[[(4-methoxy phenyl)methoxy]methyl]-3-methylcyclopentyl]-
• CAS No.: 663605-87-6
• Molecular Formula: C33H42O4Si
• Molecular Weight: 530.78
• Mol file: 663605-87-6.mol

Synonyms:

Chemical Property of Ethanone, 1-[(1S,2R,3R,4S)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-[[(4-methoxy phenyl)methoxy]methyl]-3-methylcyclopentyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethanone, 1-[(1S,2R,3R,4S)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-[[(4-methoxy phenyl)methoxy]methyl]-3-methylcyclopentyl]-

There total 14 articles about Ethanone, 1-[(1S,2R,3R,4S)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-[[(4-methoxy phenyl)methoxy]methyl]-3-methylcyclopentyl]- 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:

2-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-propane-1,2-diol → 1-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-ethanone (663605-87-6)

Guidance literature:

With sodium periodate; In water; acetone; tert-butyl alcohol; at 0 ℃; for 0.5h;

DOI:10.1002/chem.200700302

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → 1-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-ethanone (663605-87-6)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium hydroxide; dihydrogen peroxide / methanol / 3 h / 20 °C

2: trifluoroacetic acid; lithium chloride / tetrahydrofuran / 1.5 h / 0 °C

3: pyridinium p-toluenesulfonate / dichloromethane / 17 h / 20 °C

4: methanol; diethyl ether / 1 h / 0 °C

5: pyridinium p-toluenesulfonate / methanol / 15 h / 50 °C

6: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

7: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C

8: sodium hydride / N,N-dimethyl-formamide / 15 h / 20 °C

9: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2 h / 20 °C

10: sodium periodate / water; acetone; tert-butyl alcohol / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 4: Favorskii rearrangement;

DOI:10.1002/chem.200700302

Reference yield:

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone (156714-47-5) → 1-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-ethanone (663605-87-6)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridinium p-toluenesulfonate / dichloromethane / 17 h / 20 °C

2: methanol; diethyl ether / 1 h / 0 °C

3: pyridinium p-toluenesulfonate / methanol / 15 h / 50 °C

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C

6: sodium hydride / N,N-dimethyl-formamide / 15 h / 20 °C

7: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2 h / 20 °C

8: sodium periodate / water; acetone; tert-butyl alcohol / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 2: Favorskii rearrangement;

DOI:10.1002/chem.200700302

upstream raw materials:

(S)-p-mentha-6,8-dien-2-one

(S)-carvone oxide

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone

(1S,2R,3S,5S)-5-Isopropenyl-2-methyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentanecarboxylic acid methyl ester

Downstream raw materials:

2-[(1S,2R,3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-3-methyl-cyclopentyl]-pent-4-en-2-ol

trilobolide

[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol

[(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentyl]-methanol