(1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde

Base Information

• Chemical Name: (1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde
• CAS No.: 1006380-52-4
• Molecular Formula: C₂₆H₃₂O₃Si
• Molecular Weight: 420.624

Synonyms:(1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde

Chemical Property of (1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde

There total 13 articles about (1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde 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: 92.0%

((1R,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-en-1-yl)methanol (1006380-51-3) → (1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde (1006380-52-4)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; for 0.5h;

DOI:10.1021/ol7027338

Reference yield:

((1R,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-hydroxycyclohex-3-ene-1,2-diyl)dimethanol (1006380-46-6) → (1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde (1006380-52-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: camphor-10-sulfonic acid / benzene / 3 h / Inert atmosphere; Reflux

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.25 h / Inert atmosphere

3.1: cerium(III) chloride / tetrahydrofuran; pentane / 1.25 h / -78 °C / Inert atmosphere

3.2: -30 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide; toluene / 60 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / 0 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / Inert atmosphere

With cerium(III) chloride; camphor-10-sulfonic acid; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene;

DOI:10.1002/chem.201200257

Reference yield:

(R)-1-((2S,4aR,5S,8S,8aS)-8-((dimethyl(phenyl)silyl)methyl)-2-(4-methoxyphenyl)-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-5-yl)-2-(trimethylsilyl)ethanol (1006380-49-9) → (1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-enecarbaldehyde (1006380-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide; toluene / 60 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / 0 °C / Inert atmosphere

3: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / Inert atmosphere

With sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.201200257

upstream raw materials:

((1R,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-en-1-yl)methanol

(R)-1-((2S,4aR,5S,8S,8aS)-8-((dimethyl(phenyl)silyl)methyl)-2-(4-methoxyphenyl)-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-5-yl)-2-(trimethylsilyl)ethanol

(1S,2S,5S,6R)-5,6-bis((benzyloxy)methyl)-2-((dimethyl(phenyl)silyl)methyl)cyclohex-3-enol

((1R,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-hydroxycyclohex-3-ene-1,2-diyl)dimethanol

Downstream raw materials:

(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2S,5S,6S)-5-((dimethyl(phenyl)silyl)methyl)-6-((4-methoxybenzyl)oxy)-2-vinylcyclohex-3-en-1-yl)but-3-en-1-one

(S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1-((1S,2R,3S,4S,5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-4-((4-methoxybenzyl)oxy)-2-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)but-3-en-1-one

(1S,2S,4aS,7S,8S,8aR)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-7-((dimethyl(phenyl)silyl)methyl)-8-((4-methoxybenzyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol

(1R,2S,4aS,7S,8S,8aR)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-7-((dimethyl(phenyl)silyl)methyl)-8-((4-methoxybenzyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalen-1-ol

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