1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: 1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 1421640-72-3
• Molecular Formula: C₄₀H₇₄O₃Si₂
• Molecular Weight: 659.197

Synonyms:1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D₃ tert-butyldimethylsilyl ether

Chemical Property of 1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D₃ tert-butyldimethylsilyl ether

There total 8 articles about 1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin 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: 93.0%

1α,3β-bis[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methyl-9,10-secocholesta-5(10),8-dien-6-yne (1421640-70-1) → 1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D3 tert-butyldimethylsilyl ether (1421640-72-3)

Guidance literature:

With quinoline; hydrogen; In hexane; at 20 ℃; for 4.5h;

DOI:10.1021/jo302513e

Reference yield: 78.0%

C19H33IO (1421640-68-7) + 2-{(Z)-2′-[(3″S,5″R)-3″,5″-bis[(tertbutyldimethylsilyl)oxy]-2″-methylcyclohex-1″-enyl]vinyl}-4,4,5,5-tetramethyl[1,3,2]dioxaborolane → 1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D3 tert-butyldimethylsilyl ether (1421640-72-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.5b00795

Reference yield:

TB (116506-67-3) → 1α-[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methylprevitamin D3 tert-butyldimethylsilyl ether (1421640-72-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-hexyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 2.25 h / -78 - 20 °C / Inert atmosphere

2.1: lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3 h / Reflux; Darkness; Inert atmosphere

3.1: quinoline; hydrogen / hexane / 4.5 h / 20 °C

With quinoline; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; n-hexyllithium; lithium chloride; In tetrahydrofuran; hexane; 2.1: |Stille Cross Coupling;

DOI:10.1021/jo302513e

upstream raw materials:

TB

1α,3β-bis[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methyl-9,10-secocholesta-5(10),8-dien-6-yne

25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one

C₃₃H₆₆O₂Si₂Sn

Downstream raw materials:

1α,25-dihydroxy-9-methylprevitamin D₃

1α,25-dihydroxy-9α-methylvitamin D₃

1α,25-dihydroxy-9-methylene-10(S),19-dihydrovitamin D₃

1α,25-dihydroxy-9-methylene-10(R),19-dihydrovitamin D₃

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