(1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

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Chemical Name:(1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene
CAS No.:935545-34-9
Molecular Formula:C₄₁H₇₂O₄Si₂
Molecular Weight:685.191
Hs Code.:

Synonyms:(1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

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Chemical Property of (1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

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Technology Process of (1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

There total 13 articles about (1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene 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:

: 935544-88-0
(17E,8β)-8-[(tert-butyldimethylsilyl)oxy]-des-A,B-pregn-17-(20)-en-21-oic acid ethyl ester

: 935545-34-9
(1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / DIBAL-H / toluene / 14 h / -78 °C

2.1: 77 percent / Et₂Zn / toluene / 5 h / -78 - 20 °C

3.1: 91 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 7.5 h / -78 - 20 °C

4.1: MeLi / diethyl ether; tetrahydrofuran / 9.5 h / -20 - 20 °C

4.2: tetrahydrofuran; diethyl ether / 12 h / -30 °C

5.1: 92 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 0 °C

6.1: 95 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Heating

7.1: 81 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: 83 percent / tetrahydrofuran; hexane / 5 h / -78 - -40 °C

With dipyridinium dichromate; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; diethylzinc; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 2.1: Simmons-Smith reaction / 3.1: Swern oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0625195

Reference yield:

: 935544-86-8
(8β,20S)-8-[(tert-butyldimethylsilyl)oxy]-des-A,B-17α,21-cyclo-23,24-dinorcholan-22-ol

: 935545-34-9
(1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 7.5 h / -78 - 20 °C

2.1: MeLi / diethyl ether; tetrahydrofuran / 9.5 h / -20 - 20 °C

2.2: tetrahydrofuran; diethyl ether / 12 h / -30 °C

3.1: 92 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 0 °C

4.1: 95 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Heating

5.1: 81 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: 83 percent / tetrahydrofuran; hexane / 5 h / -78 - -40 °C

With dipyridinium dichromate; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Swern oxidation / 6.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0625195

Reference yield:

: 935544-90-4
(17E,8β)-8-[(tert-butyldimethylsilyl)oxy]-des-A,B-pregn-17-(20)-en-21-ol

: 935545-34-9
(1S,3R,5E,7Z,20R,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

Guidance literature:: Multi-step reaction with 7 steps

1.1: 77 percent / Et₂Zn / toluene / 5 h / -78 - 20 °C

2.1: 91 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 7.5 h / -78 - 20 °C

3.1: MeLi / diethyl ether; tetrahydrofuran / 9.5 h / -20 - 20 °C

3.2: tetrahydrofuran; diethyl ether / 12 h / -30 °C

4.1: 92 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 0 °C

5.1: 95 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Heating

6.1: 81 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 83 percent / tetrahydrofuran; hexane / 5 h / -78 - -40 °C

With dipyridinium dichromate; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; diethylzinc; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1.1: Simmons-Smith reaction / 2.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0625195