(1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene

Base Information

• Chemical Name: (1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene
• CAS No.: 112139-04-5
• Molecular Formula: C₄₂H₇₉FO₃Si₃
• Molecular Weight: 735.342
• Mol file: 112139-04-5.mol

Synonyms:(1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene

Chemical Property of (1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene

There total 17 articles about (1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene 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:

<3aR-(3aα,4β,7aβ)>-7a-methyl-4-hydroxy-octahydro-1H-inden-1-one (93489-57-7) → (1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene (112139-04-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran / 19 h / 25 °C

2: 70 percent / EtONa / ethanol / 22 h / 80 °C

3: 88 percent / H₂ / PtO₂ / ethanol / 3 h / 760 Torr

4: 1.) LDA, 2.) HMPA / 1.) THF, hexane, -30 deg C, 1 h, 2.) from -78 to 25 deg C, 2.5 h

5: 100 percent / LiAlH₄ / diethyl ether / 1.3 h / 35 °C

6: 99 percent / pyridine / 18 h / 0 °C

7: 80 percent / LiAlH₄ / tetrahydrofuran / 0.83 h / 68 °C

8: 70 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 25 °C

9: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 1.3 h / 25 °C

10: 98 percent / CH₂Cl₂ / 16 h / 25 °C

11: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 5 min, 2.) -70 deg C, 1.25 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; hydrogen; sodium ethanolate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00240a021

Reference yield:

<3aR-(3aα,4β,7aβ)>-octahydro-4-<(tetrahydro-2H-pyran-2-yl)oxy>-7a-methyl-1H-inden-1-one (112138-94-0) → (1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene (112139-04-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 70 percent / EtONa / ethanol / 22 h / 80 °C

2: 88 percent / H₂ / PtO₂ / ethanol / 3 h / 760 Torr

3: 1.) LDA, 2.) HMPA / 1.) THF, hexane, -30 deg C, 1 h, 2.) from -78 to 25 deg C, 2.5 h

4: 100 percent / LiAlH₄ / diethyl ether / 1.3 h / 35 °C

5: 99 percent / pyridine / 18 h / 0 °C

6: 80 percent / LiAlH₄ / tetrahydrofuran / 0.83 h / 68 °C

7: 70 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 25 °C

8: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 1.3 h / 25 °C

9: 98 percent / CH₂Cl₂ / 16 h / 25 °C

10: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 5 min, 2.) -70 deg C, 1.25 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; hydrogen; sodium ethanolate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00240a021

Reference yield:

<3aR-(3aα,4β,7aβ)>--7a-methyl-1H-inden-1-ylidene>acetic acid ethyl ester (112138-95-1) → (1α,3β,5Z,7E,24R)-24-fluoro-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-25-<(trimethylsilyl)oxy>-9,10-secocholesta-5,7,10(19)-triene (112139-04-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / H₂ / PtO₂ / ethanol / 3 h / 760 Torr

2: 1.) LDA, 2.) HMPA / 1.) THF, hexane, -30 deg C, 1 h, 2.) from -78 to 25 deg C, 2.5 h

3: 100 percent / LiAlH₄ / diethyl ether / 1.3 h / 35 °C

4: 99 percent / pyridine / 18 h / 0 °C

5: 80 percent / LiAlH₄ / tetrahydrofuran / 0.83 h / 68 °C

6: 70 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 25 °C

7: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 1.3 h / 25 °C

8: 98 percent / CH₂Cl₂ / 16 h / 25 °C

9: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 5 min, 2.) -70 deg C, 1.25 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; hydrogen; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00240a021

upstream raw materials:

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

<1R-<1β(1R^*,4R^*),3aα,7aβ>>-1-<4-fluoro-1,5-dimethyl-5-<(trimethylsilyl)oxy>hexyl>octahydro-7α-methyl-4H-inden-4-one

<3aR-(3aα,4β,7aβ)>-7a-methyl-4-hydroxy-octahydro-1H-inden-1-one

(R)-4-(1-ethoxyethoxy)-3-fluoro-1-iodo-4-methylpentane

Downstream raw materials:

1α,25-dihydroxy-24(R)-fluorocholecalciferol

Refernces