(3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene

Base Information

Chemical Name:(3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene
CAS No.:410080-91-0
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene

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Chemical Property of (3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene

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Technology Process of (3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene

There total 4 articles about (3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-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: 94.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 410080-90-9
(3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-5-hexen-3-ol

: 410080-91-0
(3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃; for 1.5h;
DOI:10.1139/v01-133

Reference yield:

: 144681-75-4
3-<(3,4-Dimethoxyphenyl)methoxy>propanal

: 410080-91-0
(3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuOK; n-BuLi; (-)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane; diethyl ether / 0.5 h / -78 °C

1.2: BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 4 h / -78 °C

1.3: 72 percent / NaBO₃*4H₂O; H₂O / tetrahydrofuran; hexane; diethyl ether

2.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; n-butyllithium; potassium tert-butylate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1139/v01-133

Reference yield:

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 410080-91-0
(3R,4R)-1-(3,4-dimethoxybenzyl)oxy-4-methyl-3-(tert-butyldimethylsilyl)oxy-5-hexene

Guidance literature:: Multi-step reaction with 4 steps

1.1: camphorsulfonic acid / benzene / 12 h / Heating

1.2: 37 percent / DIBAL-H / benzene; toluene / 1.08 h / 0 - 20 °C

2.1: 77 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

3.1: t-BuOK; n-BuLi; (-)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane; diethyl ether / 0.5 h / -78 °C

3.2: BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 4 h / -78 °C

3.3: 72 percent / NaBO₃*4H₂O; H₂O / tetrahydrofuran; hexane; diethyl ether

4.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 2.1: Swern oxidation;
DOI:10.1139/v01-133