(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

Base Information

Chemical Name:(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne
CAS No.:1451070-67-9
Molecular Formula:C₄₆H₈₄O₃Si₃
Molecular Weight:769.428
Hs Code.:

Synonyms:(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

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Chemical Property of (20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

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Technology Process of (20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

There total 27 articles about (20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-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: 54.0%

: 1431137-83-5
(20S)-25-[(triethylsilyl)oxy]-8-trifluoromethanesulfonyloxy-des-A,B-cholest-8-ene

: (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methyl-4-methylenecyclohexene

: 1451070-67-9
(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

Guidance literature:: With copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; diethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h; Inert atmosphere;

Reference yield: 54.0%

: (20S)-25-[(triethylsilyl)oxy]-8-trifluoromethanesulfonyloxy-des-A,B-cholest-8-ene

: (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methyl-4-methylene-cyclohexene

: 1451070-67-9
(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

Guidance literature:: With copper(l) iodide; Pd(PPh₃)(OAc)2; citric acid; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.5b01295

Reference yield:

: (1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-6-oxabicyclo[3.2.1]octan-7-one

: 1451070-67-9
(20S)-1α,3β-bis[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(triethylsilyl)oxy]-9,10-secocholesta-5(10),8-dien-6-yne

Guidance literature:: Multi-step reaction with 9 steps

1: methanol / 17 h / 20 °C / Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane / 1 h / -40 °C

3: Martins sulfurane / tetrachloromethane / 0.5 h / 20 °C / Inert atmosphere

4: diethyl ether / 2 h / 20 °C / Darkness

5: dimethyl sulfoxide / 32 h / 125 °C / Inert atmosphere

6: diisobutylaluminium hydride / toluene; dichloromethane / 2 h / -78 °C / Inert atmosphere

7: dipyridinium dichromate / dichloromethane / 4 h / 20 °C

8: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

9: copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; diethylamine / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; copper(l) iodide; dipyridinium dichromate; n-butyllithium; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; Martins sulfurane; diisobutylaluminium hydride; dimethyl sulfoxide; diethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;