1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: 1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 146698-79-5
• Molecular Formula: C₃₉H₇₀O₃Si₂
• Molecular Weight: 643.154

Synonyms:1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D₃ tert-butyldimethylsilyl ether

Chemical Property of 1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

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Technology Process of 1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D₃ tert-butyldimethylsilyl ether

There total 6 articles about 1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D₃ tert-butyldimethylsilyl ether 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: 79.0%

25-hydroxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate (134458-36-9) + (3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene (146728-45-2) → 1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D3 tert-butyldimethylsilyl ether (146698-79-5)

Guidance literature:

With diethylamine; copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

DOI:10.1021/jo00059a048

Reference yield:

(3R,5S)-3,5-dihydroxy-1-ethynyl-2-methylcyclohex-1-ene (146728-48-5) → 1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D3 tert-butyldimethylsilyl ether (146698-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

2: 79 percent / diethylamine / Pd(PPh₃)2(OAc)2, CuI / dimethylformamide / 1.5 h / Ambient temperature

With 1H-imidazole; diethylamine; copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate; In N,N-dimethyl-formamide;

DOI:10.1021/jo00059a048

Reference yield:

(3R,5S)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene (146698-82-0) → 1β-<(tert-Butyldimethylsilyl)oxy>-6,7-dehydro-25-hydroxy-3-epiprevitamin D3 tert-butyldimethylsilyl ether (146698-79-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol / 0 °C

2: imidazole / dimethylformamide

3: 79 percent / diethylamine / Pd(PPh₃)2(OAc)2, CuI / dimethylformamide / 1.5 h / Ambient temperature

With 1H-imidazole; sodium methylate; diethylamine; copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00059a048

upstream raw materials:

25-hydroxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate

(3R,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

(3R,5S)-3,5-dihydroxy-1-ethynyl-2-methylcyclohex-1-ene

(1R,2S,4R,6R)-2-Ethenyl-2-hydroxy-4-isopropenyl-1-methyl-7-oxabicyclo<4.1.0>heptane

Downstream raw materials:

1β,25-Dihydroxy-6,7-dehydro-3-epiprevitamin D₃

1-Oxo-25-hydroxy-3-epiprevitamin D₃

(5Z,7E)-(1R,3S,20R)-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene-1,3,25-triol

(1S,3S)-5-{(Z)-2-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-vinyl}-4-methyl-cyclohex-4-ene-1,3-diol

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