[(5S)-3-[(E)-[(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]methyl]-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-5-yl]oxy-tert-butyl-dimethylsilane

Base Information

• Chemical Name: [(5S)-3-[(E)-[(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]methyl]-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-5-yl]oxy-tert-butyl-dimethylsilane
• CAS No.: 251445-16-6
• Molecular Formula: C₃₄H₅₈O₃SSi
• Molecular Weight: 574.984
• DSSTox Substance ID: DTXSID20454869
• Mol file: 251445-16-6.mol

Synonyms:251445-16-6;[(5S)-3-[(E)-[(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]methyl]-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-5-yl]oxy-tert-butyl-dimethylsilane;DTXSID20454869;ISXKXFGJQNACAU-NYGAKBRBSA-N;(1,1-Dimethylethyl)dimethyl[[(1alpha,7E,22E)-6,19-sulfonyl-9,10-secoergosta-5(10),7,22-trien-3-yl]oxy]silane

Chemical Property of [(5S)-3-[(E)-[(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]methyl]-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-5-yl]oxy-tert-butyl-dimethylsilane

Chemical Property:

• PSA: 51.75000
• LogP: 10.36230
• Solubility.: Dichloromethane, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 574.38759342
• Heavy Atom Count: 39
• Complexity: 1100

Purity/Quality:

97% ^*data from raw suppliers

(3S)-tert-ButyldimethylsilylVitaminD2SO2Adduct(MixtureofDiastereomers) ^*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=CC3C4=C(CCC(C4)O[Si](C)(C)C(C)(C)C)CS3(=O)=O)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\C3C4=C(CC[C@@H](C4)O[Si](C)(C)C(C)(C)C)CS3(=O)=O)C
• Uses: Vitamin D2 intermediate.

Technology Process of [(5S)-3-[(E)-[(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]methyl]-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-5-yl]oxy-tert-butyl-dimethylsilane

There total 16 articles about [(5S)-3-[(E)-[(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]methyl]-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-5-yl]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: 97.0%

Calciferol (50-14-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 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)

Guidance literature:

Calciferol; With sulfur dioxide; In water; toluene; at 20 ℃; for 12h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2021.114005

Reference yield: 55.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (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) → (3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2 adduct (87417-26-3,251445-16-6) + (3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2-adduct (87417-26-3,87417-27-4,251445-16-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1248/cpb.43.189

Reference yield: 55.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (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) → (3S,6R)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2 adduct (87417-26-3,251445-16-6) + (3S,6S)-(tert-butyldimethylsilyloxy)-9,10-seco-ergosta-5,7(E),10(19),22(E)-tetraene SO2-adduct (87417-26-3,87417-27-4,251445-16-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1248/cpb.43.189

upstream raw materials:

tert-butyldimethylsilyl chloride

(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

(7Z)-Vitamin D₂

Calciferol

Downstream raw materials:

(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

3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct

3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct