(5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene

Base Information

• Chemical Name: (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene
• CAS No.: 239100-37-9
• Molecular Formula: C₆₀H₁₂₀O₆Si₅
• Molecular Weight: 1078.04

Synonyms:(5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene

Chemical Property of (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene

Chemical Property:

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Technology Process of (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene

There total 18 articles about (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-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: 36.0%

(4R,5S,6R)-4,6-di(tertbutyldimethylsilyloxy)-5-[3-(t-butyldimethylsilyloxy)propoxy]-7-octen-2-yne (239100-35-7) + (1R,3aR,4S,7aR)-4-[(E)-bromomethylene]-1-[(1R,4R)-4,5-di(tert-butyldimethylsilyloxy)-1,5-dimethylhexyl]-7a-methyloctahydro-1H-inden (239100-34-6) → (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10(19)-triene (239100-37-9)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; triphenylphosphine; In toluene; for 6h; Heating;

DOI:10.1016/S0039-128X(00)00149-5

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10(19)-triene (239100-37-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

2: 96 percent / lithium aluminum hydride / tetrahydrofuran / 1.5 h

3: 96 percent / N-methylmorpholine N-oxide; 4A molecular sieves; tetrapropylammonium perruthenate / CH₂Cl₂ / 2.5 h / 20 °C

4: 49 percent / sodium hexamethyldilazide / tetrahydrofuran / 1 h / 20 °C

5: 36 percent / triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾*chloroform; triethylamine / toluene / 6 h / Heating

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0039-128X(00)00149-5

Reference yield:

(2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate (77522-15-7) → (5Z,7E)-(1R,2R,3R,24R)-1,3,24-tris(tert-butyldimethylsilyloxy)-2-(3-tertbutyldimethylsilyloxypropoxy)-9,10-secocholesta-5,7,10(19)-triene (239100-37-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 71 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

2: 97 percent / sodium amalgam / tetrahydrofuran; methanol / 15 h / 20 °C

3: TsOH / acetone / 15 h / 20 °C

4: pyridine; 4-dimethylaminopyridine / 4 h / 20 °C

5: 61 percent / I₂ / methanol / 4.5 h / Heating

6: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

7: 96 percent / lithium aluminum hydride / tetrahydrofuran / 1.5 h

8: 96 percent / N-methylmorpholine N-oxide; 4A molecular sieves; tetrapropylammonium perruthenate / CH₂Cl₂ / 2.5 h / 20 °C

9: 49 percent / sodium hexamethyldilazide / tetrahydrofuran / 1 h / 20 °C

10: 36 percent / triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾*chloroform; triethylamine / toluene / 6 h / Heating

With pyridine; 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; iodine; sodium hexamethyldisilazane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; toluene;

DOI:10.1016/S0039-128X(00)00149-5

upstream raw materials:

(4R,5S,6R)-4,6-di(tertbutyldimethylsilyloxy)-5-[3-(t-butyldimethylsilyloxy)propoxy]-7-octen-2-yne

(1R,3aR,4S,7aR)-4-[(E)-bromomethylene]-1-[(1R,4R)-4,5-di(tert-butyldimethylsilyloxy)-1,5-dimethylhexyl]-7a-methyloctahydro-1H-inden

t-butyldimethylsiyl triflate

(2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate

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