(1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol

Base Information

• Chemical Name: (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol
• CAS No.: 183072-25-5
• Molecular Formula: C₃₇H₆₂O₆Si
• Molecular Weight: 630.981
• Mol file: 183072-25-5.mol

Synonyms:(1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol

Chemical Property of (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol

There total 9 articles about (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-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: 49.0%

1-Chloromethyl-2,5-bis-methoxymethoxy-3-methyl-benzene + (1aS,1bR,3aR,5S,7aR,7bS,9aR)-9a-(tert-Butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-one (182880-79-1) → (1aS,1bR,3aR,4S,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol (182880-82-6) + (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol (183072-25-5)

Guidance literature:

With lithium; In tetrahydrofuran; at 0 - 5 ℃; for 1h; Irradiation;

DOI:10.1021/jo980311g

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol (183072-25-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / LDA

2: 1.) LDA / 1.) THF, -78 deg C, 1 h, then room temp., 1 h, 2.) THF, -78 deg C to room temp., 3 h

3: 92 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 1 h / Heating

4: 1.) NaH / 1.) THF, 0 deg C, 45 min, then room temp., 10 min, 2.) THF, room temp., 30 min

5: 98 percent / Et₃N / CH₂Cl₂ / 1 h / -78 °C

6: 97 percent / propylene oxide / toluene / 168 h / 190 - 195 °C

7: 92 percent / diethylzinc / toluene; hexane / 2 h

8: 1.) Te, NaBH₄, 2.) NaOMe / 1.) EtOH, pentane, reflux, 1.5 h, 2.) THF, MeOH, 1 h

9: 49 percent / Li / tetrahydrofuran / 1 h / 0 - 5 °C / Irradiation

With tellurium; sodium tetrahydroborate; diethylzinc; sodium methylate; pyridinium p-toluenesulfonate; lithium; sodium hydride; triethylamine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;

DOI:10.1021/jo980311g

Reference yield:

6-methyl-carvone (158930-44-0) → (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol (183072-25-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) LDA / 1.) THF, -78 deg C, 1 h, then room temp., 1 h, 2.) THF, -78 deg C to room temp., 3 h

2: 92 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 1 h / Heating

3: 1.) NaH / 1.) THF, 0 deg C, 45 min, then room temp., 10 min, 2.) THF, room temp., 30 min

4: 98 percent / Et₃N / CH₂Cl₂ / 1 h / -78 °C

5: 97 percent / propylene oxide / toluene / 168 h / 190 - 195 °C

6: 92 percent / diethylzinc / toluene; hexane / 2 h

7: 1.) Te, NaBH₄, 2.) NaOMe / 1.) EtOH, pentane, reflux, 1.5 h, 2.) THF, MeOH, 1 h

8: 49 percent / Li / tetrahydrofuran / 1 h / 0 - 5 °C / Irradiation

With tellurium; sodium tetrahydroborate; diethylzinc; sodium methylate; pyridinium p-toluenesulfonate; lithium; sodium hydride; triethylamine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;

DOI:10.1021/jo980311g

upstream raw materials:

(1aS,1bR,3aR,5S,7aR,7bS,9aR)-9a-(tert-Butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-one

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

6-methyl-carvone

3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal

Downstream raw materials:

stypodiol