(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

Base Information

• Chemical Name: (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
• CAS No.: 663605-95-6
• Molecular Formula: C₃₉H₆₂O₆Si₂
• Molecular Weight: 683.089

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 22 articles about (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 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: 92.0%

(4S,4aR,5R,6S,7aS,8S,9aS)-6-(tert-Butyl-diphenyl-silanyloxy)-8-methoxymethoxy-3,5,8-trimethyl-4-triethylsilanyloxy-4a,5,6,7,7a,8,9,9a-octahydro-4H-azuleno[6,5-b]furan-2-one (663605-94-5) → (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)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; Heating;

DOI:10.1002/anie.200353140

Reference yield:

C40H64O5Si2 (663605-91-2) → (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)

Guidance literature:

Multi-step reaction with 5 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

With 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:

(S)-carvone epoxide (672898-50-9) → (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)

Guidance literature:

Multi-step reaction with 20 steps

1: trifluoroacetic acid; lithium chloride / tetrahydrofuran / 20 °C

2: pyridinium p-toluenesulfonate / dichloromethane / 20 °C

3: sodium methylate / 0 °C

4: pyridinium p-toluenesulfonate / methanol / 40 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

6: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

7: sodium hydride / N,N-dimethyl-formamide / 20 °C

8: osmium(VIII) oxide; N-methyl-2-indolinone; water / acetone / 20 °C

9: sodium periodate / 20 °C

10: tetrahydrofuran / -78 °C

11: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

12: phosphate buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C / pH 7

13: N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve / dichloromethane / 20 °C

14: tert.-butyl lithium / tetrahydrofuran / -78 °C

15: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

16: Grubbs' dihydroimidazoline ruthenium catalyst / dichloromethane / Heating

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

18: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

19: sodium hydride / tetrahydrofuran / Heating

20: lithium borohydride / tetrahydrofuran / Heating

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; N-methyl-2-indolinone; phosphate buffer; tetrapropylammonium perruthennate; potassium dioxotetrahydroxoosmate(VI); 4 A molecular sieve; water; tert.-butyl lithium; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; potassium hexacyanoferrate(III); methanesulfonamide; Grubbs' dihydroimidazoline ruthenium catalyst; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 3: Favorskii rearrangement / 19: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/anie.200353140

upstream raw materials:

(4S,4aR,5R,6S,7aS,8S,9aS)-6-(tert-Butyl-diphenyl-silanyloxy)-8-methoxymethoxy-3,5,8-trimethyl-4-triethylsilanyloxy-4a,5,6,7,7a,8,9,9a-octahydro-4H-azuleno[6,5-b]furan-2-one

(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

C₄₀H₆₄O₅Si₂

(S)-carvone epoxide

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

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