(3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene

Base Information

Chemical Name:(3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene
CAS No.:240821-03-8
Molecular Formula:C₃₉H₅₈O₅Si₂
Molecular Weight:663.058
Hs Code.:

Synonyms:(3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene

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Chemical Property of (3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene

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Technology Process of (3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene

There total 8 articles about (3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene 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: 99.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 252006-16-9
2-[3-(tert-butyl-diphenyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-2-methyl-propyl]-but-3-en-1-ol

: 240821-03-8
(3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1248/cpb.47.1288

Reference yield:

: 91751-24-5,92817-88-4,123284-89-9,112897-04-8
(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

: 240821-03-8
(3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / TiCl₄; iso-Pr₂EtN / CH₂Cl₂ / 3 h / 0 °C

2: LiBH₄ / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

3: aq. NaOH / diethyl ether

4: 99 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

5: 93 percent / DIBAH / hexane; toluene / 1 h / -35 °C

6: 99 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; sodium hydroxide; lithium borohydride; camphor-10-sulfonic acid; titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1: Condensation / 2: Reduction / 3: Hydrolysis / 4: Substitution / 5: reductive ring opening / 6: Condensation;
DOI:10.1248/cpb.47.1288

Reference yield:

: 240821-01-6
(2S,3S,4R)-5-tert-butyldiphenylsilyloxy-4-methyl-2-vinylpentane-1,3-diole

: 240821-03-8
(3S,4S,5R)-3-(tert-butyldimethylsilyloxymethyl)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

2: 93 percent / DIBAH / hexane; toluene / 1 h / -35 °C

3: 99 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; camphor-10-sulfonic acid; diisobutylaluminium hydride; In hexane; dichloromethane; toluene; 1: Substitution / 2: reductive ring opening / 3: Condensation;
DOI:10.1248/cpb.47.1288