[(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane

Base Information

• Chemical Name: [(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane
• CAS No.: 87649-56-7
• Molecular Formula: C33H58OSi
• Molecular Weight: 498.908
• DSSTox Substance ID: DTXSID301118893
• Mol file: 87649-56-7.mol

Synonyms:87649-56-7;DTXSID301118893;AC-31106;Silane, (1,1-dimethylethyl)dimethyl[[(3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-yl]oxy]-

Chemical Property of [(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane

Chemical Property:

• PSA: 9.23000
• LogP: 10.64850
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 9
• Exact Mass: 498.42569300
• Heavy Atom Count: 35
• Complexity: 794

Purity/Quality:

>98% ^*data from raw suppliers

VitaminD3O-t-ButyldimethylsilylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O[Si](C)(C)C(C)(C)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O[Si](C)(C)C(C)(C)C)C
• Uses: Vitamin D3 t-Butyldimethylsilyl Ether is an impurity of Vitamin D3 (V676045), which is the vitamin that mediates intestinal calcium absorbtion, bone calcium metabolism and probably, muscle activity. It occurs in and is isolated from fish liver oils. Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor superfamily. It modulates the proliferation and differentiation of both normal and cancer cells. It also has antiproliferative and antimetastatic effects on breast, colon, and prostate cancer cells. Activated vitamin D receptors in intestine and bone maintain calcium absorbance and homeostasis. Vitamin D3 t-Butyldimethylsilyl Ether is also an intermediate in synthesizing (7Z)-Calcipotriene (C144225), which is an isomeric impurity of Calcipotriene (14

Technology Process of [(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane

There total 37 articles about [(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl]oxy-tert-butyl-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%

tert-butyldimethylsilyl chloride (18162-48-6) + (5E)-cholecalciferol (67-97-0,7489-19-2,22350-41-0,57651-82-8,57651-83-9,98744-46-8,98818-17-8) → tert-Butyl-{(S)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane (87649-55-6,87649-56-7,101565-48-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1021/jo00359a061

Reference yield:

vitamin D3 (67-97-0) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyl-{(S)-3-[2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane (87649-56-7)

Guidance literature:

With 1H-imidazole; 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; at 20 ℃;

Reference yield:

{(S)-3-[1-Bromo-meth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-tert-butyl-dimethyl-silane (502495-32-1) + (8E)-8-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-methylene]-de-A,B-cholestane (502495-33-2) → tert-Butyl-{(S)-3-[2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane (87649-56-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; In tetrahydrofuran; water; at 60 ℃;

DOI:10.1021/ol0274007

upstream raw materials:

Acetic acid 1-[(1R,3aR,7aR)-4-benzenesulfonyl-1-(1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-yl]-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl ester

(2Z)-2-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>-ethanol

(2Z)-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>acetaldehyde

(=)-*α-phenylsulfonyl-des-AB-cholestane

Downstream raw materials:

1α-hydroxycholecalciferol

(1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol

vitamin D₃ 3,5-dinitrobenzoate

vitamin D₃

Refernces

• 1、 Hanazawa, Takeshi,Koyama, Akiko,Wada, Takeshi,Morishige, Eiko,Okamoto, Sentaro,Sato, Fumie. "Efficient convergent synthesis of 1alpha,25-dihydroxyvitamin D3 and its analogues by Suzuki-Miyaura coupling.". . p. 523 - 525. Retrieved 2007/10/03.
• 2、 Nemoto, Hideo,Kurobe, Hiroshi,Fukumoto, Keiichiro,Kametani, Tetsuji. "A Novel Approach to the Stereocontrolled Synthesis of Steroid Side Chains Including the CD-Ring System: The First Total Synthesis of (+)-8α-(Phenylsulfonyl)des-AB-cholestane and Its Efficient Conversion into Grundmann's Ketone and Vitamin D3". . p. 5311 - 5320. Retrieved 2007/10/02.