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

Base Information

• Chemical Name: (20S)-3-desoxy-1α-[(tert-butyldiphenylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-vitamin D₃
• CAS No.: 1431619-87-2
• Molecular Formula: C₅₀H₇₆O₂Si₂
• Molecular Weight: 765.323

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

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

Chemical Property:

Purity/Quality:

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

There total 20 articles about (20S)-3-desoxy-1α-[(tert-butyldiphenylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-vitamin D₃ 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: 64.0%

C50H76O2Si2 → (20S)-3-desoxy-1α-[(tert-butyldiphenylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-vitamin D3 (1431619-87-2)

Guidance literature:

at 40 - 65 ℃; Inert atmosphere;

Reference yield: 64.0%

C50H76O2Si2 → (20S)-3-desoxy-1α-[(tert-butyldiphenylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-vitamin D3 (1431619-87-2)

Guidance literature:

In hexane; at 40 - 65 ℃; Inert atmosphere;

DOI:10.1021/jm500750b

Reference yield:

(2R,3S,4S)-2-hydroxy-3-methyl-4-pivaloyloxy-cyclohexanone (1431137-92-6) → (20S)-3-desoxy-1α-[(tert-butyldiphenylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-vitamin D3 (1431619-87-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: silver nitrate / N,N-dimethyl-formamide / 30 h / 20 °C / Inert atmosphere

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

2.2: 4 h / -78 - 20 °C

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

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

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

5.2: 0.75 h / -78 - 0 °C

6.1: Martins sulfurane / tetrachloromethane / 6 h / 20 °C / Inert atmosphere

6.2: 19 h / 20 °C / Inert atmosphere

7.1: copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; diethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

8.1: quinoline; hydrogen / hexane / 0.5 h / 20 °C

9.1: 40 - 65 °C / Inert atmosphere

With quinoline; copper(l) iodide; n-butyllithium; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; Martins sulfurane; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; silver nitrate; diethylamine; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.2: |Wittig Olefination;

upstream raw materials:

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

1-(1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-inden-4-one

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

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

Downstream raw materials:

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

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