(3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal)

Base Information

• Chemical Name: (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal)
• CAS No.: 474432-41-2
• Molecular Formula: C₃₆H₆₂O₃Si
• Molecular Weight: 570.972
• Mol file: 474432-41-2.mol

Synonyms:(3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal)

Chemical Property of (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal)

There total 7 articles about (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal) 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: 73.0%

(S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide (100858-27-3) + (24R)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal) (474432-39-8) → (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal) (474432-41-2)

Guidance literature:

(S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 5h;

(24R)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal); In tetrahydrofuran; hexane; at 20 ℃; for 5h; Further stages.;

DOI:10.1002/1521-3765(20020617)8:12<2747::AID-CHEM2747>3.0.CO;2-J

Reference yield:

(1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol (226569-00-2) → (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal) (474432-41-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / aq. H₂SO₄ / acetone / 2.5 h / ultrasonication

2.1: 99 percent / PDC / CH₂Cl₂ / 6 h

3.1: nBuLi / hexane; tetrahydrofuran / 5 h / -78 - 0 °C

3.2: 73 percent / tetrahydrofuran; hexane / 5 h / 20 °C

With dipyridinium dichromate; n-butyllithium; sulfuric acid; In tetrahydrofuran; hexane; dichloromethane; acetone; 3.1: Wittig-Horner reaction / 3.2: Wittig-Horner reaction;

DOI:10.1002/1521-3765(20020617)8:12<2747::AID-CHEM2747>3.0.CO;2-J

Reference yield:

(8β,24R)-de-A,B-cholesta-8,24,25-triol cyclic 24,25-(1-methylethylidene acetal) (239100-24-4) → (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal) (474432-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / PDC / CH₂Cl₂ / 6 h

2.1: nBuLi / hexane; tetrahydrofuran / 5 h / -78 - 0 °C

2.2: 73 percent / tetrahydrofuran; hexane / 5 h / 20 °C

With dipyridinium dichromate; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; 2.1: Wittig-Horner reaction / 2.2: Wittig-Horner reaction;

DOI:10.1002/1521-3765(20020617)8:12<2747::AID-CHEM2747>3.0.CO;2-J

upstream raw materials:

(S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide

(24R)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal)

(1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol

(8β,24R)-de-A,B-cholesta-8,24,25-triol cyclic 24,25-(1-methylethylidene acetal)

Downstream raw materials:

24(R),25-dihydroxycholecalciferol