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

Base Information

• Chemical Name: 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methyl-9,10-secocholesta-5(10),8-dien-6-yne
• CAS No.: 1421640-70-1
• Molecular Formula: C₄₀H₇₂O₃Si₂
• Molecular Weight: 657.181
• Mol file: 1421640-70-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methyl-9,10-secocholesta-5(10),8-dien-6-yne 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: 92.0%

C19H33IO (1421640-68-7) + TB (116506-67-3) → 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methyl-9,10-secocholesta-5(10),8-dien-6-yne (1421640-70-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; at 0 - 20 ℃; for 4h; Darkness;

DOI:10.1021/jo302513e

Reference yield: 83.0%

C33H66O2Si2Sn (1421640-71-2) + C19H33IO (1421640-68-7) → 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methyl-9,10-secocholesta-5(10),8-dien-6-yne (1421640-70-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; In tetrahydrofuran; for 3h; Reflux; Darkness; Inert atmosphere;

DOI:10.1021/jo302513e

Reference yield:

(1R,3aR,5R,7aR)-1-[(R)-1’,5’-dimethyl-5’-[(triethylsilyl)oxy]hexyl]-5,7a-dimethyloctahydroinden-4-one (1421640-67-6) → 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-25-hydroxy-9-methyl-9,10-secocholesta-5(10),8-dien-6-yne (1421640-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrazine / ethanol; water / 2 h / Reflux

2.1: iodine; 1,1,3,3-tetramethylguanidine / toluene / 2 h / 20 °C

2.2: 20 °C

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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1,3,3-tetramethylguanidine; iodine; lithium chloride; hydrazine; In tetrahydrofuran; ethanol; water; toluene; 3.1: |Stille Cross Coupling;

DOI:10.1021/jo302513e

upstream raw materials:

TB

C₁₉H₃₃IO

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

C₃₃H₆₆O₂Si₂Sn

Downstream raw materials:

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

1α,25-dihydroxy-9-methylprevitamin D₃

1α,25-dihydroxy-9α-methylvitamin D₃

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