3-O-(tert-Butyldimethylsilyl)-5,6-trans-vitamin D2

Base Information

• Chemical Name: 3-O-(tert-Butyldimethylsilyl)-5,6-trans-vitamin D2
• CAS No.: 104846-63-1
• Molecular Formula: C₃₄H₅₈OSi
• Molecular Weight: 510.919
• DSSTox Substance ID: DTXSID301098697
• Mol file: 104846-63-1.mol

Synonyms:104846-63-1;3-O-(tert-Butyldimethylsilyl)-5,6-trans-vitamin D2;tert-butyl((E)-3-((E)-2-((1R,3aS,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexyloxy)dimethylsilane;[(1S,3E)-3-[(2E)-2-[(1R,3As,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane;tert-Butyl (((S,E)-3-(2-((1R,3aS,7aR,E)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexyl)oxy)dimethylsilane;DTXSID301098697;CS-M1909;AKOS037650120;CS-14308;(1R,3aS,4E,7aR)-4-[(2E)-2-[(5S)-5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethylidene]octahydro-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-1H-indene;tert-Butyl(((S,E)-3-(2-((1R,3aS,7aR,E)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexyl)oxy)dimethylsilane

Chemical Property of 3-O-(tert-Butyldimethylsilyl)-5,6-trans-vitamin D2

Chemical Property:

• Boiling Point: 540.5±39.0 °C(Predicted)
• PSA: 9.23000
• Density: 0.93±0.1 g/cm3(Predicted)
• LogP: 10.67050
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Dichloromethane, Dimethyl Sulfoxide, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 510.42569300
• Heavy Atom Count: 36
• Complexity: 866

Purity/Quality:

99% ^*data from raw suppliers

3-O-(tert-Butyldimethylsilyl)-5,6-trans-vitaminD2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O[Si](C)(C)C(C)(C)C)C
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(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: Protected 5,6-trans-Vitamin D2 (V676060), the main decomposition product of Vitamin D2 (V676040).

Technology Process of 3-O-(tert-Butyldimethylsilyl)-5,6-trans-vitamin D2

There total 12 articles about 3-O-(tert-Butyldimethylsilyl)-5,6-trans-vitamin D2 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: 94.0%

SO2-adduct of 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-secoergosta-5,7(E),10(19),22(E)-tetraene (170081-43-3,251445-16-6) → (5E)-vitamin D2 tert-butyldimethylsilyl ether (104846-62-0,104846-63-1)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 1.25h; Heating;

DOI:10.1021/jo00058a034

Reference yield:

Calciferol (50-14-6) → (5E)-vitamin D2 tert-butyldimethylsilyl ether (104846-62-0,104846-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: SO₂ / CH₂Cl₂ / 1.25 h / -10 °C

2: imidazole / Ambient temperature

3: 94 percent / NaHCO₃ / aq. ethanol / 1.25 h / Heating

With 1H-imidazole; sulfur dioxide; sodium hydrogencarbonate; In ethanol; dichloromethane;

DOI:10.1021/jo00058a034

Reference yield:

(S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol (87680-65-7) → (5E)-vitamin D2 tert-butyldimethylsilyl ether (104846-62-0,104846-63-1)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / Ambient temperature

2: 94 percent / NaHCO₃ / aq. ethanol / 1.25 h / Heating

With 1H-imidazole; sodium hydrogencarbonate; In ethanol;

DOI:10.1021/jo00058a034

upstream raw materials:

3β-hydroxy-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene

tert-butyldimethylsilyl chloride

(3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene SO₂ adduct

(3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene SO₂-adduct

Downstream raw materials:

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene

(6R)-SO₂ adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10⁽¹⁹⁾-triene

(6S)-SO₂ adduct of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10⁽¹⁹⁾-triene

(6S)- and (6R)-SO₂ adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene

Refernces

• 1、 Anderson, Bruce G.,Bauta, William E.,Cantrell, William R.. "Development of an improved process for doxercalciferol via a continuous photochemical reaction". experimental part. p. 967 - 975. Retrieved 2012/08/27.
• 2、 Cota, J. G.,Meilan, M. C.,Mourino, A.,Castedo, L.. "Hydrotitanation-Protonation of Vitamin D2 and Its Analogues: An Efficient Method for the Preparation of 10,19-Dihydrovitamins D2 Including Dihydrotachysterol2". . p. 6094 - 6099. Retrieved 2007/10/02.