(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

Base Information

Chemical Name:(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde
CAS No.:1428946-46-6
Molecular Formula:C₂₁H₄₀O₃Si₂
Molecular Weight:396.718
Hs Code.:

Synonyms:(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

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Chemical Property of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

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Technology Process of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

There total 16 articles about (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-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: 79.0%

: [(3’R,5’R)-3’,5’-bis[(tert-butyldimethylsilyl)oxy]-2’-methyl-4’-methylene-cyclohex-1’-enyl]methanol

: 1428946-46-6
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

Guidance literature:: With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/acs.jmedchem.5b01295

Reference yield:

: (1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-6-oxabicyclo[3.2.1]octan-7-one

: 1428946-46-6
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: methanol / 17 h / 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -40 °C

3.1: Martins sulfurane / tetrachloromethane / 0.5 h / 20 °C / Inert atmosphere

4.1: diethyl ether / 2 h / 20 °C / Darkness

5.1: N,N-dimethyl-formamide / 6 h / 125 °C / Inert atmosphere

5.2: 2 h / -78 °C / Inert atmosphere

6.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C

With 2,6-dimethylpyridine; dipyridinium dichromate; Martins sulfurane; In methanol; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/acs.jmedchem.5b01295

Reference yield:

: 213250-59-0
methyl (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexanecarboxylate

: 1428946-46-6
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-4-methylene-cyclohex-1-enecarbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: Martins sulfurane / tetrachloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: diethyl ether / 2 h / 20 °C / Darkness

3.1: N,N-dimethyl-formamide / 6 h / 125 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

4.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C

With dipyridinium dichromate; Martins sulfurane; In tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/acs.jmedchem.5b01295