Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester

Base Information

• Chemical Name: Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester
• CAS No.: 663606-12-0
• Molecular Formula: C₄₁H₆₄O₇Si₂
• Molecular Weight: 725.126
• Mol file: 663606-12-0.mol

Synonyms:Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester

Chemical Property of Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester

There total 23 articles about Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl 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: 95.0%

acetic anhydride (108-24-7) + (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-Butyl-diphenyl-silanyloxy)-7-[2-hydroxy-1-methyl-eth-(E)-ylidene]-4-methoxymethoxy-1,4-dimethyl-8-triethylsilanyloxy-decahydro-azulen-6-ol (663605-95-6) → Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester (663606-12-0)

Guidance literature:

With 2,6-dimethylpyridine; dmap; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.200353140

Reference yield:

C40H64O5Si2 (663605-91-2) → Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester (663606-12-0)

Guidance literature:

Multi-step reaction with 6 steps

1: Grubbs' dihydroimidazoline ruthenium catalyst / dichloromethane / Heating

2: potassium dioxotetrahydroxoosmate(VI); sodium hydrogencarbonate; potassium hexacyanoferrate(III) / methanesulfonamide; potassium carbonate / tert-butyl alcohol / 20 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

4: sodium hydride / tetrahydrofuran / Heating

5: lithium borohydride / tetrahydrofuran / Heating

6: 2,6-dimethylpyridine; dmap / dichloromethane / 20 °C

With 2,6-dimethylpyridine; dmap; lithium borohydride; potassium dioxotetrahydroxoosmate(VI); sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hexacyanoferrate(III); methanesulfonamide; Grubbs' dihydroimidazoline ruthenium catalyst; potassium carbonate; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 4: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/anie.200353140

Reference yield:

(1R,2S,3aS,4S,8S,8aR)-2-(tert-Butyl-diphenyl-silanyloxy)-7-ethoxy-4-methoxymethoxy-1,4-dimethyl-8-triethylsilanyloxy-1,2,3,3a,4,5,8,8a-octahydro-azulene (663605-92-3) → Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester (663606-12-0)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium dioxotetrahydroxoosmate(VI); sodium hydrogencarbonate; potassium hexacyanoferrate(III) / methanesulfonamide; potassium carbonate / tert-butyl alcohol / 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

3: sodium hydride / tetrahydrofuran / Heating

4: lithium borohydride / tetrahydrofuran / Heating

5: 2,6-dimethylpyridine; dmap / dichloromethane / 20 °C

With 2,6-dimethylpyridine; dmap; lithium borohydride; potassium dioxotetrahydroxoosmate(VI); sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 3: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/anie.200353140

upstream raw materials:

acetic anhydride

(1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-Butyl-diphenyl-silanyloxy)-7-[2-hydroxy-1-methyl-eth-(E)-ylidene]-4-methoxymethoxy-1,4-dimethyl-8-triethylsilanyloxy-decahydro-azulen-6-ol

(1R,2S,3aS,4S,8S,8aR)-2-(tert-Butyl-diphenyl-silanyloxy)-7-ethoxy-4-methoxymethoxy-1,4-dimethyl-8-triethylsilanyloxy-1,2,3,3a,4,5,8,8a-octahydro-azulene

(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-8-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-5-one

Downstream raw materials:

trilobolide

nortrilobolide

(2aS,5aS,7S,7aS,9S,10R,10aR,10bS,10cR)-9-(tert-Butyl-diphenyl-silanyloxy)-7,10c-dihydroxy-2a,4,4,7,10-pentamethyl-decahydro-1,3,5-trioxa-benzo[cd]cyclopenta[h]azulen-2-one

(3S,3aR,4S,6S,6aS,8S,9R,9aR,9bS)-8-(tert-Butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-4,6-bis-methoxymethoxy-3,6,9-trimethyl-decahydro-azuleno[4,5-b]furan-2-one