2-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2l6-benzo[c]thiophen-1-ylmethylene]-7a-methyl-octahydro-inden-1-yl}-propan-1-ol

Base Information

• Chemical Name: 2-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2l6-benzo[c]thiophen-1-ylmethylene]-7a-methyl-octahydro-inden-1-yl}-propan-1-ol
• CAS No.: 344798-31-8
• Molecular Formula: C₂₈H₄₈O₄SSi
• Molecular Weight: 508.838
• Mol file: 344798-31-8.mol

Synonyms:2-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2l6-benzo[c]thiophen-1-ylmethylene]-7a-methyl-octahydro-inden-1-yl}-propan-1-ol

Chemical Property of 2-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2l6-benzo[c]thiophen-1-ylmethylene]-7a-methyl-octahydro-inden-1-yl}-propan-1-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.536
• Boiling Point: 600.859°C at 760 mmHg
• Flash Point: 317.188°C
• PSA: 71.98000
• Density: 1.107g/cm³
• LogP: 7.50630

Purity/Quality:

(βS,1R,3aS,4E,7aR)-4-[[(6S)-6-[[(tert-Butyldimethylsilyloxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]methylene]octahydro-β,7a-dimethyl-1H-Indene-1-ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (βS,1R,3aS,4E,7aR)-4-[[(6S)-6-[[(tert-Butyldimethylsilyloxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]methylene]octahydro-β,7a-dimethyl-1H-Indene-1-ethanol is an intermediate in the synthesis of Secalciferol (S211500), metabolite of Vitamin D, a possible anti-inflammatory steroid.

Technology Process of 2-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2l6-benzo[c]thiophen-1-ylmethylene]-7a-methyl-octahydro-inden-1-yl}-propan-1-ol

There total 6 articles about 2-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2l6-benzo[c]thiophen-1-ylmethylene]-7a-methyl-octahydro-inden-1-yl}-propan-1-ol 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: 67.0%

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) → 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct (344798-31-8)

Guidance literature:

With sodium tetrahydroborate; ozone; In methanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2021.114005

Reference yield:

3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene (866453-60-3) → 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct (344798-31-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -25 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/op010229e

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct (344798-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) SO₂

2: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -10 deg C, 2.) room temperature, 2 h

With sodium tetrahydroborate; sulfur dioxide; ozone;

DOI:10.1021/jo00125a051

upstream raw materials:

SO2-adduct of 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-secoergosta-5,7(E),10(19),22(E)-tetraene

Calciferol

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

Downstream raw materials:

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

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

3(S)-<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene

ethyl 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate