Tert-butyl-[(1R,3S,5Z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane

Base Information

• Chemical Name: Tert-butyl-[(1R,3S,5Z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane
• CAS No.: 81522-68-1
• Molecular Formula: C33H51 O3 P Si2
• Molecular Weight: 582.911
• DSSTox Substance ID: DTXSID00456023
• Nikkaji Number: J1.810.504G,J513.853A,J335.994H
• Wikidata: Q72446923
• Mol file: 81522-68-1.mol

Synonyms:81522-68-1;Tert-butyl-[(1R,3S,5Z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane;CID 11124745;Phosphine oxide, [2-[3,5-bis [[(1,1-dimethylethyl) dimethylsily]oxy]-2-methylenecyclohexylidene]ethyl]diphenyl-,[3s-(1z,3a,5b0)];Phosphineoxide,[2-[3,5-bis[[(1,1-dimethylethyl)dimethylsily]oxy]-2-methylenecyclohexylidene]ethyl]diphenyl-,[3s-(1z,3a,5b0)];((Z)-2-((3S,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethyl)diphenylphosphine oxide;SCHEMBL3211756;DTXSID00456023;BCP14765;CS-M1835;MFCD08703326;AKOS015964462;AC-8891;AS-75150;((Z)-2-((3R,5S)-3,5-BIS((TERT-BUTYLDIMETHYLSILYL)OXY)-2-METHYLENECYCLOHEXYLIDENE)ETHYL)DIPHENYLPHOSPHINEOXIDE;[2-[(Z)-2-Methylene-3beta,5alpha-bis(tert-butyldimethylsiloxy)cyclohexylidene]ethyl]diphenylphosphine oxide;{(2Z)-2-[(3S,5R)-3,5-Bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidenecyclohexylidene]ethyl}(oxo)diphenyl-lambda~5~-phosphane;2-[(1E,3S)-3beta,5alpha-Bis(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyldiphenylphosphine oxide;2-[2-Methylene-3beta,5alpha-bis(tert-butyldimethylsiloxy)cyclohexylidene]ethyldiphenylphosphine oxide;3S-(1Z,3A,5B)-2-[3,5-Bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]ethyldiphenylphosphine oxide;Phosphine oxide, [(2Z)-2-[(3S,5R)-3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethyl]diphenyl-;Phosphine oxide,[(2Z)-2-[(3S,5R)-3,5-bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-2-Methylenecyclohexylidene]ethyl]diphenyl-;tert-butyl({[(1R,3S,5Z)-3-[(tert-butyldimethylsilyl)oxy]-5-[2-(diphenylphosphoroso)ethylidene]-4-methylidenecyclohexyl]oxy})dimethylsilane

Chemical Property of Tert-butyl-[(1R,3S,5Z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane

Chemical Property:

• Boiling Point: 571.9±50.0 °C(Predicted)
• PSA: 45.34000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 9.05770
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 582.31143555
• Heavy Atom Count: 39
• Complexity: 890

Purity/Quality:

99% ^*data from raw suppliers

[(2Z)-2-[(3S,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphineOxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(C(=C)C(=CCP(=O)(C2=CC=CC=C2)C3=CC=CC=C3)C1)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](C(=C)/C(=C\CP(=O)(C2=CC=CC=C2)C3=CC=CC=C3)/C1)O[Si](C)(C)C(C)(C)C
• Uses: [(2Z)-2-[(3S,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine Oxide is used as a reagent in the preparation of hydroxymethylated dihydroxyvitamin D3 analogs which have antitumor and transactivation activity.

Technology Process of Tert-butyl-[(1R,3S,5Z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane

There total 39 articles about Tert-butyl-[(1R,3S,5Z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane 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: 95.0%

(1R,3S)-1,3-bis((tert-butyl)dimethylsilanyloxy)-5-[2-(diphenylphosphinoyl)ethylene]-4-methylenecyclohexane (145554-08-1) → [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1)

Guidance literature:

With 9-fluorenone; tert-butyl methyl ether; for 3h; Irradiation;

DOI:10.1021/ol006982u

Reference yield: 93.0%

{2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane (127492-07-3) → [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; at 25 ℃;

DOI:10.1021/ja00374a052

Reference yield: 50.0%

<3S-(1Z,3α,5β)>-2-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>-1-chloroethane (81506-25-4) + Diphenylphosphine oxide (4559-70-0) → [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1)

Guidance literature:

Diphenylphosphine oxide; With potassium hydroxide; tetrabutylammomium bromide; In tert-butyl methyl ether; water; at 20 ℃; for 0.25h;

<3S-(1Z,3α,5β)>-2-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>-1-chloroethane; In tert-butyl methyl ether; water; at 20 ℃; for 2.08333 - 2.16667h;

upstream raw materials:

<3S-(1Z,3α,5β)>-2-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>-1-chloroethane

lithium diphenylphosphide

{2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

(1R,3S)-1,3-bis((tert-butyl)dimethylsilanyloxy)-5-[2-(diphenylphosphinoyl)ethylene]-4-methylenecyclohexane

Downstream raw materials:

(S)-4-((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-2,2,4-trimethyl-[1,3]dioxolane

(1R,3aR,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene

(R)-5-{(1R,3aR,7aR)-4-[2-[(3S,5R)-3,5-Dihydroxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-yl}-hexanal

(20S)-1α-<(tert-butyldimethylsilyl)oxy>-16-en-25-<(methoxymethyl)oxy>vitamin D₃ tert-butyldimethylsilyl ether

Refernces

• 1、 Daniewski, Andrzej R.,Garofalo, Lisa M.,Kabat, Marek M.. "Improved preparation of A-ring phosphine oxides for the synthesis of vitamin D analogs". . p. 3031 - 3039. Retrieved 2007/10/03.
• 2、 Hijikuro,Doi,Takahashi. "Parallel synthesis of a vitamin D3 library in the solid-phase". . p. 3716 - 3722. Retrieved 2007/10/03.