[(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane

Base Information

• Chemical Name: [(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane
• CAS No.: 1432905-89-9
• Molecular Formula: C₅₀H₉₈O₄Si₄
• Molecular Weight: 881.62

Synonyms:[(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane

Chemical Property of [(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane

There total 8 articles about [(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane 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: 60.0%

(1R,3aR,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxy-hexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-one (1432905-97-9) + [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) → [(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane (1432905-89-9)

Guidance literature:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.25h; Inert atmosphere;

(1R,3aR,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxy-hexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-one; In tetrahydrofuran; at -65 ℃; Inert atmosphere;

DOI:10.1021/jm400032t

Reference yield:

(1R,3aR,7aR)-7a-methyl-1-[(1S)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxy-hexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-one (1432905-95-7) → [(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane (1432905-89-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: cyclohexane / 6.5 h / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -70 °C / Inert atmosphere

2.2: -65 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; cyclohexane;

DOI:10.1021/jm400032t

Reference yield:

(R)-6-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]-7-iodo-2-methylheptan-2-ol (713521-95-0) → [(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1R)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxyhexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylenecyclohexoxy]tert-butyldimethylsilane (1432905-89-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: zinc; pyridine; nickel(II) chloride hexahydrate / 0.67 h / 50 - 65 °C / Inert atmosphere

1.2: 20 °C / Cooling with ice; Inert atmosphere

2.1: diethyl ether / 20 °C / Cooling with ice; Inert atmosphere

3.1: fluorosilicic acid / acetonitrile / 15 h / Inert atmosphere

4.1: dipyridinium dichromate / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 4 h / Inert atmosphere

5.1: cyclohexane / Inert atmosphere

6.1: cyclohexane / 6.5 h / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -70 °C / Inert atmosphere

7.2: -65 °C / Inert atmosphere

With pyridine; dipyridinium dichromate; n-butyllithium; fluorosilicic acid; nickel(II) chloride hexahydrate; zinc; In tetrahydrofuran; diethyl ether; hexane; cyclohexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile;

DOI:10.1021/jm400032t

upstream raw materials:

(1R,3aR,7aR)-7a-methyl-1-[(1S)-6,6,6-trideuterio-1-(4-methyl-4-trimethylsilyloxy-pentyl)-5-(trideuteriomethyl)-5-trimethylsilyloxy-hexyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-one

(R)-2-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]-6-methylheptane-1,6-diol

(R)-6-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]-7-iodo-2-methylheptan-2-ol

ethyl (5S)-5-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-9-hydroxy-9-methyl-decanoate

Downstream raw materials:

1α,25-dihydroxy-21-(3-hydroxy-3-methyl-but-1-yl)-26,27-hexadeuterio-cholecalciferol

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