4-[[(6S)-6-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]Methylene]octahydro-α,7a-diMethyl-1H-indene-1-acetaldehyde

Base Information

• Chemical Name: 4-[[(6S)-6-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]Methylene]octahydro-α,7a-diMethyl-1H-indene-1-acetaldehyde
• CAS No.: 866453-60-3
• Molecular Formula: C₂₈H₄₆O₄SSi
• Molecular Weight: 506.822
• Mol file: 866453-60-3.mol

Synonyms:3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10⁽¹⁹⁾-triene

Chemical Property of 4-[[(6S)-6-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]Methylene]octahydro-α,7a-diMethyl-1H-indene-1-acetaldehyde

Chemical Property:

Purity/Quality:

4-[[(6S)-6-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]methylene]octahydro-α,7a-dimethyl-1H-indene-1-acetaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 4-[[(6S)-6-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]methylene]octahydro-α,7a-dimethyl-1H-indene-1-acetaldehyde is an intermediate in the synthesis of Secalciferol (S211500), metabolite of Vitamin D, a possible anti-inflammatory steroid.

Technology Process of 4-[[(6S)-6-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]Methylene]octahydro-α,7a-diMethyl-1H-indene-1-acetaldehyde

There total 2 articles about 4-[[(6S)-6-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-1,3,4,5,6,7-hexahydro-2,2-dioxidobenzo[c]thien-1-yl]Methylene]octahydro-α,7a-diMethyl-1H-indene-1-acetaldehyde 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:

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-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene (866453-60-3)

Guidance literature:

SO2-adduct of 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-secoergosta-5,7(E),10(19),22(E)-tetraene; With ozone; In methanol; dichloromethane; at -60 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -60 - 20 ℃;

Reference yield:

Calciferol (50-14-6) → 3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene (866453-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfur dioxide / dichloromethane / 3 h / -78 - -10 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane / 5 - 20 °C / Inert atmosphere

3: sodium acetate; acetic acid; ozone / methanol; dichloromethane / -25 °C / Inert atmosphere

With 1H-imidazole; sulfur dioxide; sodium acetate; ozone; acetic acid; In methanol; dichloromethane;

DOI:10.1021/op010229e

Reference yield: 97.0%

3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10(19)-triene (866453-60-3) → C28H46O2Si

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 2h; Reflux;

DOI:10.1021/ol101879k

upstream raw materials:

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

Calciferol

Downstream raw materials:

3(R)-(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5(Z),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

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