2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane

Base Information

• Chemical Name: 2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane
• CAS No.: 194208-59-8
• Molecular Formula: C₄₆H₈₂O₆Si₂
• Molecular Weight: 787.324
• Mol file: 194208-59-8.mol

Synonyms:2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane

Chemical Property of 2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane

There total 13 articles about 2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane 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: 78.0%

TB (116506-67-3) + Trifluoro-methanesulfonic acid (1R,3aR,6R,7aR)-6-(2-[1,3]dioxolan-2-yl-ethyl)-1-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl ester (139619-84-4) → 2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane (194208-59-8)

Guidance literature:

With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 70 - 75 ℃; for 2h;

DOI:10.1016/S0040-4039(00)77685-4

Reference yield:

4-bromo-2-methyl-2-butanol (35979-69-2) → 2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane (194208-59-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 76 percent / dimethylsulfoxide / 1.5 h / 90 - 100 °C

2: 1.) NaH / 1.) DMF, 0 deg C, 1.5 h 2.) DMF, room temperature, overnight

3: 1.) LDA / 1.) hexanes, THF, -78 deg C, 30 min 2.) hexanes, THF, -78 deg c - 1 h, room temperature - overnight

4: 90 percent / K, t-BuOH / diethyl ether; hexamethylphosphoric acid triamide / 12 h / 0 - 20 °C

5: 99 percent / pyridinium dichromate, pyridinium tosylate / CH₂Cl₂ / 12 h / 0 °C

6: 1.) LDA / 1.) hexanes, THF, -78 deg C - 1 h, room temperature - 1 h, 2.) hexanes, THF, -78 deg C - room temperature, overnight

7: 0.922 g / palladium ⁽²⁾ acetate / acetonitrile / 20 h

9: 1.) MeLi / 1.) Et₂O, THF, room temperature, 25 min, 2.) Et₂O, THF, -78 deg C - room temperature, overnight

10: 78 percent / Et₃N, bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 75 °C

With bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; dipyridinium dichromate; methyllithium; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; tert-butyl alcohol; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(97)00692-3

Reference yield:

4-hydroxy-4-methylpentanenitrile (6789-52-2) → 2-{2-[(3R,3aR,5R,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane (194208-59-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 1.5 h 2.) DMF, room temperature, overnight

2: 1.) LDA / 1.) hexanes, THF, -78 deg C, 30 min 2.) hexanes, THF, -78 deg c - 1 h, room temperature - overnight

3: 90 percent / K, t-BuOH / diethyl ether; hexamethylphosphoric acid triamide / 12 h / 0 - 20 °C

4: 99 percent / pyridinium dichromate, pyridinium tosylate / CH₂Cl₂ / 12 h / 0 °C

5: 1.) LDA / 1.) hexanes, THF, -78 deg C - 1 h, room temperature - 1 h, 2.) hexanes, THF, -78 deg C - room temperature, overnight

6: 0.922 g / palladium ⁽²⁾ acetate / acetonitrile / 20 h

8: 1.) MeLi / 1.) Et₂O, THF, room temperature, 25 min, 2.) Et₂O, THF, -78 deg C - room temperature, overnight

9: 78 percent / Et₃N, bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 75 °C

With bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; dipyridinium dichromate; methyllithium; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; tert-butyl alcohol; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(97)00692-3

upstream raw materials:

TB

Trifluoro-methanesulfonic acid (1R,3aR,6R,7aR)-6-(2-[1,3]dioxolan-2-yl-ethyl)-1-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl ester

2-bromo-2-(2-ethyl)dioxolane

4-bromo-2-methyl-2-butanol

Downstream raw materials:

2-{2-[(3R,3aR,5R,7aR)-7-{(Z)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-ethyl}-[1,3]dioxolane

(1R,3S)-5-[2-[(1R,3aS,6S,7aR)-6-(3,3-Dimethoxy-propyl)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol

2-{2-[(3R,3aR,5S,7aS)-7-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-3-((R)-5-methoxymethoxy-1,5-dimethyl-hexyl)-3a-methyl-octahydro-inden-5-yl]-ethyl}-[1,3]dioxolane