(1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane

Base Information

Chemical Name:(1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane
CAS No.:239089-29-3
Molecular Formula:C₁₉H₂₈O₅
Molecular Weight:336.428
Hs Code.:

Synonyms:(1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane

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Chemical Property of (1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane

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Technology Process of (1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane

There total 8 articles about (1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane 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:

: 239089-28-2
5-Formyl-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane

: 1730-25-2
allylmagnesium bromide

: 239089-29-3
(1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane

Guidance literature:: With B-chlorodiisopinocampheylborane; In diethyl ether; at -98 ℃; for 1h;
DOI:10.1016/S0040-4039(99)00755-8

Reference yield:

: 770-74-1
2,2-dimethyl-5,5-bis(hydroxymethyl)-1,3-dioxane

: 239089-29-3
(1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.5 h / 25 °C

1.2: 35.1 g / dimethylformamide / 0.67 h / 25 °C

2.1: 19 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 25 °C

3.1: 88 percent / DIBALH / CH₂Cl₂ / 0.67 h / 25 °C

4.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 25 °C

5.1: (+)-DIPCl / diethyl ether / 1 h / -78 °C

5.2: diethyl ether / 1 h / -93 °C

With water; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; B-chlorodiisopinocampheylborane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Etherification / 2.1: Cyclization / 3.1: Ring cleavage / 4.1: Oxidation / 5.1: Substitution / 5.2: Addition;
DOI:10.1055/s-2000-8224

Reference yield:

: 51335-75-2
2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester

: 239089-29-3
(1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 15.4 g / LAH / diethyl ether / 1 h / 25 °C

2.1: NaH / dimethylformamide / 0.5 h / 25 °C

2.2: 35.1 g / dimethylformamide / 0.67 h / 25 °C

3.1: 19 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 25 °C

4.1: 88 percent / DIBALH / CH₂Cl₂ / 0.67 h / 25 °C

5.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 25 °C

6.1: (+)-DIPCl / diethyl ether / 1 h / -78 °C

6.2: diethyl ether / 1 h / -93 °C

With lithium aluminium tetrahydride; water; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; B-chlorodiisopinocampheylborane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Metallation / 2.2: Etherification / 3.1: Cyclization / 4.1: Ring cleavage / 5.1: Oxidation / 6.1: Substitution / 6.2: Addition;
DOI:10.1055/s-2000-8224