(3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene

Base Information

• Chemical Name: (3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene
• CAS No.: 1431617-98-9
• Molecular Formula: C₂₉H₃₈OSi₂
• Molecular Weight: 458.791

Synonyms:(3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene

Chemical Property of (3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene

There total 15 articles about (3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene 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:

(1R,2S,3R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilanyl)ethynyl]-cyclohexanol (1431617-89-8) → (3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene (1431617-98-9) + (5R,6R)-5-[(tert-butyldiphenylsilyl)oxy]-6-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene

Guidance literature:

With Martins sulfurane; In tetrachloromethane; at 20 ℃; for 6h; Overall yield = 81 %; Overall yield = 62 mg; Inert atmosphere;

Reference yield:

(2R,3S,4S)-2-hydroxy-3-methyl-4-pivaloyloxy-cyclohexanone (1431137-92-6) → (3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene (1431617-98-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: silver nitrate / N,N-dimethyl-formamide / 17 h / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 0 - 20 °C

2.2: 5 h / -78 - 20 °C

3.1: diisobutylaluminium hydride / toluene; dichloromethane / 1.5 h / -78 - -40 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 0.75 h / -78 - 0 °C

6.1: tetrachloromethane; Martins sulfurane / 6 h / Inert atmosphere

With tetrachloromethane; n-butyllithium; Martins sulfurane; diisobutylaluminium hydride; Dess-Martin periodane; silver nitrate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.2: |Wittig Olefination;

DOI:10.1021/jm500750b

Reference yield:

(2R,3R,4S)-2-[(tert-butyldiphenylsilyl)oxy]-3-methyl-1-methylene-4-pivaloyloxy-cyclohexane (1431617-86-5) → (3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methyl-4-methylene-1-[(trimethylsilyl)ethynyl]-cyclohexene (1431617-98-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / toluene; dichloromethane / 1.5 h / -78 - -40 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 0.75 h / -78 - 0 °C

4.1: tetrachloromethane; Martins sulfurane / 6 h / Inert atmosphere

With tetrachloromethane; n-butyllithium; Martins sulfurane; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/jm500750b

upstream raw materials:

7-methyl-1,4-dioxa-spiro[4.5]decan-8-ol

(2R,3S,4S)-2-hydroxy-3-methyl-4-pivaloyloxy-cyclohexanone

(2R,3R,4S)-2-[(tert-butyldiphenylsilyl)oxy]-3-methyl-4-pivaloyloxy-cyclohexanone

(2R,3R,4S)-2-[(tert-butyldiphenylsilyl)oxy]-3-methyl-1-methylene-4-pivaloyloxy-cyclohexane

Downstream raw materials:

(20R)-3-desoxy-1α,25-dihydroxy-2-methylene-vitamin D₃

(20S)-3-desoxy-1α,25-dihydroxy-2-methylene-vitamin D₃

3-desoxy-1α-[(tert-butyldiphenylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-vitamin D₃

(20S)-3-desoxy-1α-[(tert-butyldiphenylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-vitamin D₃

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