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

Base Information

• Chemical Name: Acetic acid (R)-2-[(2S,3R,3aR,4S,5R,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester
• CAS No.: 663605-97-8
• Molecular Formula: C₄₃H₇₀O₁₀Si₂
• Molecular Weight: 803.194
• Mol file: 663605-97-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 28 articles about Acetic acid (R)-2-[(2S,3R,3aR,4S,5R,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-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:

Acetic acid 2-[(2S,3R,3aR,4S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-octahydro-azulen-(5E)-ylidene]-propyl ester (663605-96-7) → Acetic acid (R)-2-[(2S,3R,3aR,4S,5R,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester (663605-97-8) + Acetic acid (S)-2-[(2S,3R,3aR,4S,5S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester

Guidance literature:

With Quinuclidine; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tert-butyl alcohol; at 20 ℃;

DOI:10.1002/anie.200353140

Reference yield:

(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-1-methoxymethoxy-1-methyl-but-3-enyl)-2-methyl-cyclopentanecarbaldehyde (663606-11-9) → Acetic acid (R)-2-[(2S,3R,3aR,4S,5R,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester (663605-97-8) + Acetic acid (S)-2-[(2S,3R,3aR,4S,5S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester

Guidance literature:

Multi-step reaction with 10 steps

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

2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

3: Grubbs' dihydroimidazoline ruthenium catalyst / dichloromethane / Heating

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

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

6: sodium hydride / tetrahydrofuran / Heating

7: lithium borohydride / tetrahydrofuran / Heating

8: 2,6-dimethylpyridine; dmap / dichloromethane / 20 °C

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

10: Quinuclidine; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III) / methanesulfonamide; potassium carbonate / tert-butyl alcohol / 20 °C

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

DOI:10.1002/anie.200353140

Reference yield:

(S)-carvone epoxide (672898-50-9) → Acetic acid (R)-2-[(2S,3R,3aR,4S,5R,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester (663605-97-8) + Acetic acid (S)-2-[(2S,3R,3aR,4S,5S,6S,8S,8aS)-2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6,8-bis-methoxymethoxy-3,8-dimethyl-4-triethylsilanyloxy-decahydro-azulen-5-yl]-2-hydroxy-propyl ester

Guidance literature:

Multi-step reaction with 23 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

21: 2,6-dimethylpyridine; dmap / dichloromethane / 20 °C

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

23: Quinuclidine; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III) / methanesulfonamide; potassium carbonate / tert-butyl alcohol / 20 °C

With Quinuclidine; 1H-imidazole; 2,6-dimethylpyridine; 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:

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

(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

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

(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