1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

Base Information

Chemical Name:1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol
CAS No.:294176-95-7
Molecular Formula:C₄₁H₇₄O₆Si₂
Molecular Weight:719.206
Hs Code.:

Synonyms:1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

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Chemical Property of 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

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Technology Process of 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

There total 8 articles about 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-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: 92.0%

: 18664-32-9
1,3-dimethoxypropan-2-one

: 167892-99-1
1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene

: 294176-95-7
1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;
DOI:10.1016/S0968-0896(00)00106-1

Reference yield:

: 143884-24-6
(5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene

: 294176-95-7
1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / dimethylsulfoxide / 0.5 h / 90 °C

2: 54 percent / DIBALH / tetrahydrofuran; hexane / -70 - 20 °C

3: 54 percent / diethyl ether / 0.17 h / 20 °C

4: 78 percent / TPAP; NMO; 4A MS / CH₂Cl₂ / 0.25 h / 20 °C

5: 41 percent / SeO₂ / CH₂Cl₂; methanol / 2 h / Heating

6: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C

7: 72 percent / Et₃N; anthracene / toluene / 1 h / Irradiation

8: 92 percent / LiN(TMS)2 / tetrahydrofuran; hexane / 0.17 h / -78 °C

With 1H-imidazole; selenium(IV) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; anthracene; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Reduction / 3: Grignard reaction / 4: Oxidation / 5: Oxidation / 6: Substitution / 7: Isomerization / 8: Condensation;
DOI:10.1016/S0968-0896(00)00106-1

Reference yield:

: 167892-93-5
3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene

: 294176-95-7
1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,27-dimethoxy-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 54 percent / diethyl ether / 0.17 h / 20 °C

2: 78 percent / TPAP; NMO; 4A MS / CH₂Cl₂ / 0.25 h / 20 °C

3: 41 percent / SeO₂ / CH₂Cl₂; methanol / 2 h / Heating

4: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C

5: 72 percent / Et₃N; anthracene / toluene / 1 h / Irradiation

6: 92 percent / LiN(TMS)2 / tetrahydrofuran; hexane / 0.17 h / -78 °C

With 1H-imidazole; selenium(IV) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; anthracene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Grignard reaction / 2: Oxidation / 3: Oxidation / 4: Substitution / 5: Isomerization / 6: Condensation;
DOI:10.1016/S0968-0896(00)00106-1