(2-((3R,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphine oxide

Base Information

• Chemical Name: (2-((3R,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphine oxide
• CAS No.: 139356-39-1
• Molecular Formula: C32H51O3PSi2
• Molecular Weight: 570.9
• DSSTox Substance ID: DTXSID00456806
• Nikkaji Number: J804.769C
• Mol file: 139356-39-1.mol

Synonyms:139356-39-1;(2-((3R,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphine oxide;(3R-trans)-[2-[3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexylidene]ethyl]diphenyl-phosphine Oxide;Phosphine oxide, [2-[(3R,5R)-3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexylidene]ethyl]diphenyl-;tert-butyl-[(1R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)cyclohexyl]oxy-dimethylsilane;Paricalcitol Impurity B;(3R,5R)-[2-[3,5-bis-(t-butyldimethyl-silanyloxy)-cyclohexylidene]-ethyl]-diphenyl-phosphine oxide;(1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane;SCHEMBL3178296;DTXSID00456806;(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene) ethyl)diphenylphosphine oxide;AMY23694;CS-M0459;MFCD18207201;AKOS027323524;CS-T-06904;AS-74888;A905336;(2-((3R,5R)-3,5-Bis((t-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphine oxide;1-[2-(Diphenylphosphinyl)ethylidene]-3beta,5alpha-bis(tert-butyldimethylsiloxy)cyclohexane;(2-((3R,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphineoxide;(3R,5R)-[2-[3,5-bis-(t-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethyl]-diphenyl-phosphine oxide;(3R,5R)-[2-[3,5-bis-(t-butyldimethylsilanyloxy)-cyclohexylidene]-ethyl]-diphenyl-phosphine oxide;(3R,5R)-[2-[3,5-Bis-(tert-butyl-dimethyl-silyloxy)-cyclohexylidene]-ethyl]-diphenyl-phosphine oxide;TERT-BUTYL({[(1R,3R)-3-[(TERT-BUTYLDIMETHYLSILYL)OXY]-5-[2-(DIPHENYLPHOSPHOROSO)ETHYLIDENE]CYCLOHEXYL]OXY})DIMETHYLSILANE

Chemical Property of (2-((3R,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphine oxide

Chemical Property:

• Boiling Point: 561.0±50.0 °C(Predicted)
• PSA: 45.34000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 8.89160
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 570.31143555
• Heavy Atom Count: 38
• Complexity: 780

Purity/Quality:

99% ^*data from raw suppliers

(3R-trans)-[2-[3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexylidene]ethyl]diphenyl-phosphineOxide ^*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(CC(=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](CC(=CCP(=O)(C2=CC=CC=C2)C3=CC=CC=C3)C1)O[Si](C)(C)C(C)(C)C
• Uses: (3R-trans)-[2-[3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexylidene]ethyl]diphenyl-phosphine Oxide is used in the preparation of Vitamin D compounds.

Technology Process of (2-((3R,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphine oxide

There total 43 articles about (2-((3R,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethyl)diphenylphosphine oxide 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%

((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) (139356-38-0) + diphenylphosphane (829-85-6) → (1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane (139356-39-1)

Guidance literature:

diphenylphosphane; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane); In tetrahydrofuran; for 3h;

Reference yield: 78.0%

C20H41IO2Si2 (1402710-05-7) + diphenylphosphane (829-85-6) → (1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane (139356-39-1)

Guidance literature:

C₂₀H₄₁IO₂Si₂; diphenylphosphane; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

With dihydrogen peroxide; In tetrahydrofuran; hexane; water; at 0 ℃; for 1h;

DOI:10.1016/j.steroids.2013.06.001

Reference yield: 75.0%

[(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol (139356-37-9) + diphenylphosphane (829-85-6) → (1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane (139356-39-1)

Guidance literature:

[(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol; With n-butyllithium; p-toluenesulfonyl chloride; In tetrahydrofuran; hexane; at 0 ℃; for 3h;

diphenylphosphane; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 2h;

With dihydrogen peroxide; In dichloromethane; at 22 ℃; for 3.5h;

DOI:10.1016/S0040-4020(00)01035-8

upstream raw materials:

((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

diphenylphosphane

lithium diphenylphosphide

[(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol

Downstream raw materials:

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

Acetic acid (S)-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester

(R)-6-{(S)-3-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-methyl-cyclohexyl}-5-methyl-hept-6-enoic acid methyl ester

C₄₃H₈₆O₃Si₃

Refernces

• 1、 -. "Preparation method of paricalcitol intermediate". Paragraph 0084; 0085; 0086; 0087. . Retrieved 2018/01/11.
• 2、 Pietraszek, Anita,Malińska, Maura,Chodyński, Michal,Krupa, Malgorzata,Krajewski, Krzysztof,Cmoch, Piotr,Wo?niak, Krzysztof,Kutner, Andrzej. "Synthesis and crystallographic study of 1,25-dihydroxyergocalciferol analogs". . p. 1003 - 1014. Retrieved 2013/10/21.