(Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

Base Information

• Chemical Name: (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol
• CAS No.: 338956-81-3
• Molecular Formula: C₂₁H₄₂O₃Si₂
• Molecular Weight: 398.734
• Mol file: 338956-81-3.mol

Synonyms:(Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

Chemical Property of (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

There total 30 articles about (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol 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: 63.0%

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol (343969-47-1) → (1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol (55812-82-3,63730-57-4,63730-58-5,102281-42-5) + (1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one (55812-80-1,55870-05-8,70144-73-9) + (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol (338956-81-3)

Guidance literature:

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol; With pyridine; lead(IV) acetate; In dichloromethane; at 0 ℃; for 1.5h;

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 1.5h;

Reference yield: 63.0%

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol (343969-47-1) → (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol (338956-81-3)

Guidance literature:

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol; With lead(IV) acetate; In dichloromethane;

With sodium tetrahydroborate; cerium(III) chloride;

DOI:10.1016/S0040-4039(01)00317-3

Reference yield: 52.0%

(Z,5R,7R)-bis(tert-butyldimethylsilyl)oxy-3-(trifluoromethanesulfonyl)oxy-2,8-nonadien-1-ol (338956-79-9) → (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol (338956-81-3)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 24.5h;

DOI:10.1016/S0968-0896(00)00259-5

upstream raw materials:

(Z,5R,7R)-bis(tert-butyldimethylsilyl)oxy-3-(trifluoromethanesulfonyl)oxy-2,8-nonadien-1-ol

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol

tert-butyldimethylsilyl chloride

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol

Downstream raw materials:

(2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde

(Z,3R,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylideneethyl]diphenylphosphine oxide

(5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene