(1S,3R,5E,7Z,20S,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,20S,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene
CAS No.:935545-45-2
Molecular Formula:C₄₁H₇₂O₄Si₂
Molecular Weight:685.191
Hs Code.:

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

There total 15 articles about (1S,3R,5E,7Z,20S,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: 93.0%

: 935545-44-1
(8β,20S,22Z)-25-[(methoxymethyl)oxy]-des-A,B-17α,21-cyclocholest-22-en-8-one

: 81522-68-1
[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

: 935545-45-2
(1S,3R,5E,7Z,20S,22Z)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene

Guidance literature:: [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(8β,20S,22Z)-25-[(methoxymethyl)oxy]-des-A,B-17α,21-cyclocholest-22-en-8-one; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 5h; Further stages.;
DOI:10.1021/jo0625195

Reference yield:

: 935545-11-2
(8β,20R)-8-[(tert-butyldimethylsilyl)oxy]-des-A,B-17α,21-cyclo-23,24-dinorcholan-22-ol

: 935545-45-2
(1S,3R,5E,7Z,20S,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 10 steps

1.1: 88 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 7.5 h / -78 - 20 °C

2.1: 96 percent / pyridine; Zn; PPh₃ / CH₂Cl₂ / 5 h

3.1: 87 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.1: 98 percent / n-BuLi; BF₃*OEt₂ / hexane; tetrahydrofuran / 6 h / 20 °C

5.1: 90 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 0 °C

6.1: 94 percent / quinoline; H₂ / Lindlar catalyst / hexane / 20 °C

7.1: 88 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 0 °C

8.1: 92 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Heating

9.1: 91 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

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

10.2: 93 percent / tetrahydrofuran; hexane / 5 h / -78 - -40 °C

With pyridine; quinoline; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0625195

Reference yield:

: 935545-18-9
(8β,20R)-8-[(tert-butyldimethylsilyl)oxy]-des-A,B-17α,21-cyclo-23,24-dinorcholan-22-al

: 935545-45-2
(1S,3R,5E,7Z,20S,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 9 steps

1.1: 96 percent / pyridine; Zn; PPh₃ / CH₂Cl₂ / 5 h

2.1: 87 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: 98 percent / n-BuLi; BF₃*OEt₂ / hexane; tetrahydrofuran / 6 h / 20 °C

4.1: 90 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 0 °C

5.1: 94 percent / quinoline; H₂ / Lindlar catalyst / hexane / 20 °C

6.1: 88 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 0 °C

7.1: 92 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Heating

8.1: 91 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

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

9.2: 93 percent / tetrahydrofuran; hexane / 5 h / -78 - -40 °C

With pyridine; quinoline; dipyridinium dichromate; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0625195