2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester

Base Information

• Chemical Name: 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester
• CAS No.: 950849-15-7
• Molecular Formula: C₄₃H₆₉O₁₀PSi₂
• Molecular Weight: 833.16
• Mol file: 950849-15-7.mol

Synonyms:2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester

Chemical Property of 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester

There total 20 articles about 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl 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:

(S)-carvone epoxide (672898-50-9) → 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester (950849-15-7)

Guidance literature:

Multi-step reaction with 18 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

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; 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;

DOI:10.1002/anie.200353140

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester (950849-15-7)

Guidance literature:

Multi-step reaction with 14 steps

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

2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

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

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

5: sodium periodate / 20 °C

6: tetrahydrofuran / -78 °C

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

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

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

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

11: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

12: Grubbs' dihydroimidazoline ruthenium catalyst / dichloromethane / Heating

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

14: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

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

DOI:10.1002/anie.200353140

Reference yield:

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone (156714-47-5) → 2-(Diethoxy-phosphoryl)-propionic acid (1R,2S,3aS,4S,6S,8S,8aR)-2-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-1,4-dimethyl-7-oxo-8-triethylsilanyloxy-decahydro-azulen-6-yl ester (950849-15-7)

Guidance literature:

Multi-step reaction with 17 steps

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

2: sodium methylate / 0 °C

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

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

5: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C

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

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

8: sodium periodate / 20 °C

9: tetrahydrofuran / -78 °C

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

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

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

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

14: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

15: Grubbs' dihydroimidazoline ruthenium catalyst / dichloromethane / Heating

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

17: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; 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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); methanesulfonamide; Grubbs' dihydroimidazoline ruthenium catalyst; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 2: Favorskii rearrangement;

DOI:10.1002/anie.200353140

upstream raw materials:

2-(diethylphosphono)propionic acid

(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

(S)-carvone epoxide

tert-butylchlorodiphenylsilane

Downstream 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

(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

(2S,3R,3aR,4S,5S,6S,8S,8aS)-2-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-1,2-dihydroxy-1-methyl-ethyl)-6,8-bis-methoxymethoxy-3,8-dimethyl-decahydro-azulene-4,5-diol