(2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one

Base Information

• Chemical Name: (2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one
• CAS No.: 946524-47-6
• Molecular Formula: C₂₆H₅₂O₂Si₂
• Molecular Weight: 452.869
• Mol file: 946524-47-6.mol

Synonyms:(2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one

Chemical Property of (2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one

There total 1 articles about (2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one 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: 89.0%

(E)-(3-iodo-1-methyl-1-propenyl)-trimethylsilane (52685-51-5) + (2S,5R)-5-methyl-2-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-cyclohexan-1-one (166317-79-9) → (2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one (946524-47-6)

Guidance literature:

(2S,5R)-5-methyl-2-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-cyclohexan-1-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

(E)-(3-iodo-1-methyl-1-propenyl)-trimethylsilane; With diethylzinc; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ol070992e

Reference yield: 87.0%

(2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one (946524-47-6) + vinyl magnesium bromide (1826-67-1) → (1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol (946524-49-8)

Guidance literature:

vinyl magnesium bromide; With cerium(III) chloride; In tetrahydrofuran; at -78 ℃;

(2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one; In tetrahydrofuran; at -78 - -15 ℃; Further stages.;

DOI:10.1021/ol070992e

Reference yield:

(2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one (946524-47-6) → C19H36O2Si (946524-58-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: 0.316 g / potassium carbonate; MeOH

3.1: 93 percent / hydrogen; pyridine / Pd on BaSO₄ / methanol / 18 h

4.1: 0.076 g / conc. HCl / methanol / 2 h / 0 °C

With pyridine; hydrogenchloride; methanol; n-butyllithium; hydrogen; potassium carbonate; palladium on barium sulfate; In tetrahydrofuran; methanol;

DOI:10.1021/ol070992e

upstream raw materials:

(E)-(3-iodo-1-methyl-1-propenyl)-trimethylsilane

(2S,5R)-5-methyl-2-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-cyclohexan-1-one

Downstream raw materials:

(1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

C₁₇H₃₀O₂

C₂₈H₅₄O₂Si₂

C₁₉H₃₆O₂Si