(2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Base Information

Chemical Name:(2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane
CAS No.:638222-34-1
Molecular Formula:C₃₀H₅₀O₆Si
Molecular Weight:534.809
Hs Code.:

Synonyms:(2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane

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Chemical Property of (2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane

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Technology Process of (2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane

There total 17 articles about (2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane 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: 77.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 445422-98-0
(2R,4S,6S,8R,10S)-8-(2-ethylallyl)-10-methoxy-2-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecan-4-ol

: 638222-34-1
(2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1039/b504148a

Reference yield:

: (2R,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecan-4-ol

: 74-88-4
methyl iodide

: 638222-34-1
(2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ol035848h

Reference yield:

: 445423-04-1
(2R,4R,6R)-2-benzyloxy-8-ethyl-6-propionoxy-8-nonen-4-ol

: 638222-34-1
(2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 90 percent / proton-sponge / CH₂Cl₂ / 3 h / 0 °C

2.1: 88 percent / K₂CO₃ / methanol / 48 h / 20 °C

3.1: 95 percent / imidazole / dimethylformamide / 16 h / 20 °C

4.1: 99 percent / lithium 4,4'-di(tert-butyl)biphenylide / tetrahydrofuran / 1.5 h / -78 °C

5.1: 97 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.67 h / 20 °C

6.1: Et₃N / diethyl ether / 1 h / 0 °C

7.1: diethyl ether / 17.5 h / -78 - -20 °C

7.2: 110.8 mg / aq. H₂O₂; methanol / diethyl ether / 1 h / 20 °C

8.1: aq. HF / acetonitrile / 0.67 h / 0 °C

8.2: 23.8 mg / HCl / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

9.1: 77 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; Proton-Sponge; hydrogen fluoride; potassium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5.1: Dess-Martin oxidation;
DOI:10.1039/b504148a