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

Base Information

• Chemical Name: 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
• CAS No.: 139619-82-2
• Molecular Formula: C₄₆H₈₄O₆Si₂
• Molecular Weight: 789.34

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 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

There total 13 articles about 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 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: 80.0%

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) → 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 (139619-82-2)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In hexane; for 4.5h; Ambient temperature;

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

Reference yield:

4-hydroxy-4-methylpentanenitrile (6789-52-2) → 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 (139619-82-2)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH / dimethylformamide / 12 h / Ambient temperature

2: 1) LDA / 1) THF, -78 deg C, 30 min, 2) -78 deg C, 1 h, then rt, 12 h

3: 90 percent / K, t-BuOH, HMPA / diethyl ether / 10 h / Ambient temperature

4: 99 percent / pyridinium dichromate, PPTS / CH₂Cl₂

5: 1) LDA / 1) THF, -78 deg C, 15 min, then -78 deg C -> rt, 2 h, 2) -78 deg C, 15 min

6: Pd(OAc)2 / acetonitrile / 12 h / Ambient temperature

7: 1) CuBr*Me₂S, Me₂S / 1) THF, -78 deg C, 45 min, 2) THF, -78 deg C, 2 h, then rt, 12 h

8: 1) MeLi / 1) THF, rt, 25 min, 2) rt, 12 h

9: 78 percent / NEt₃ / (Ph₃P)2PdCl₂ / dimethylformamide / 2 h / 70 - 75 °C

10: 80 percent / H₂, quinoline / Lindlar catalyst / hexane / 4.5 h / Ambient temperature

With quinoline; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; dipyridinium dichromate; copper(I) bromide dimethylsulfide complex; dimethylsulfide; methyllithium; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; tert-butyl alcohol; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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-{(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 (139619-82-2)

Guidance literature:

Multi-step reaction with 11 steps

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

2: NaH / dimethylformamide / 12 h / Ambient temperature

3: 1) LDA / 1) THF, -78 deg C, 30 min, 2) -78 deg C, 1 h, then rt, 12 h

4: 90 percent / K, t-BuOH, HMPA / diethyl ether / 10 h / Ambient temperature

5: 99 percent / pyridinium dichromate, PPTS / CH₂Cl₂

6: 1) LDA / 1) THF, -78 deg C, 15 min, then -78 deg C -> rt, 2 h, 2) -78 deg C, 15 min

7: Pd(OAc)2 / acetonitrile / 12 h / Ambient temperature

8: 1) CuBr*Me₂S, Me₂S / 1) THF, -78 deg C, 45 min, 2) THF, -78 deg C, 2 h, then rt, 12 h

9: 1) MeLi / 1) THF, rt, 25 min, 2) rt, 12 h

10: 78 percent / NEt₃ / (Ph₃P)2PdCl₂ / dimethylformamide / 2 h / 70 - 75 °C

11: 80 percent / H₂, quinoline / Lindlar catalyst / hexane / 4.5 h / Ambient temperature

With quinoline; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; dipyridinium dichromate; copper(I) bromide dimethylsulfide complex; dimethylsulfide; methyllithium; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; tert-butyl alcohol; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

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

4-bromo-2-methyl-2-butanol

4-hydroxy-4-methylpentanenitrile

1,3-dioxolan-2-ylethylmagnesium bromide

Downstream raw materials:

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

(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

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