(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

Base Information

Chemical Name:(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol
CAS No.:189102-63-4
Molecular Formula:C₃₃H₅₄O₅
Molecular Weight:530.789
Hs Code.:

(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

Synonyms:(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

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Chemical Property of (1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

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Technology Process of (1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

There total 13 articles about (1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol 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: 25.0%

: C₄₅H₈₂O₅Si₂

: 189102-64-5
(1R,5R)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

: 189102-63-4
(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

Guidance literature:: With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; for 12h; Ambient temperature;
DOI:10.1021/jo970049w

Reference yield:

: 50-14-6
Calciferol

: 189102-63-4
(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) O₃, O₂, NaHCO₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 7.5 psi, 2.0 h, 2.) 0 deg C, 3 h.

2: Py / 1.) -25 deg C, 3.5 h, 2.) 0 deg C, 20 h.

3: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

4: 80 percent / NaHCO₃, DMSO / 150 °C

5: 55 percent / O₂, t-BuOK / 2-methyl-propan-2-ol / 0.25 h

6: 67 percent / NaBH₄ / methanol / 0 °C

7: 1.) KH / 1.) THF, room temperature, 15 min, 2.) THF, reflux, 2.5 h.

8: tetrabutylammonium fluoride hydrate, molecular sieves 4 Angstroem / tetrahydrofuran / 1 h / Ambient temperature

9: 100 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

10: 1.) PhLi / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 5 h.

11: 25 percent / TBAF, molecular sieves 4 Angstroeme / tetrahydrofuran / 12 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; oxygen; potassium hydride; sodium hydrogencarbonate; ozone; dimethyl sulfoxide; phenyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jo970049w

Reference yield:

: 66774-80-9,111924-49-3
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

: 189102-63-4
(1S,5S)-3-[2-[(1S,3aS,7aS)-1-{(R)-1-[2-((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-ethyl}-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-hydroxymethyl-4-methylene-cyclohexanol

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

2: 80 percent / NaHCO₃, DMSO / 150 °C

3: 55 percent / O₂, t-BuOK / 2-methyl-propan-2-ol / 0.25 h

4: 67 percent / NaBH₄ / methanol / 0 °C

5: 1.) KH / 1.) THF, room temperature, 15 min, 2.) THF, reflux, 2.5 h.

6: tetrabutylammonium fluoride hydrate, molecular sieves 4 Angstroem / tetrahydrofuran / 1 h / Ambient temperature

7: 100 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

8: 1.) PhLi / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 5 h.

9: 25 percent / TBAF, molecular sieves 4 Angstroeme / tetrahydrofuran / 12 h / Ambient temperature

With 2,6-dimethylpyridine; sodium tetrahydroborate; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; oxygen; potassium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; phenyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jo970049w