(1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

Base Information

Chemical Name:(1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one
CAS No.:139278-51-6
Molecular Formula:C₃₇H₆₉NO₄Si₂
Molecular Weight:648.13
Hs Code.:

(1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

Synonyms:(1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

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Chemical Property of (1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

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Technology Process of (1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

There total 3 articles about (1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one 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: 80.0%

: 139278-50-5
(E)-3-methyl-2,5-bis(triisopropylsiloxy)-1,3-pentadiene

: 139402-50-9
(1R,4S)-4,7,7-Trimethyl-2-(2-methyl-acryloyl)-2-aza-bicyclo[2.2.1]heptan-3-one

: 139278-51-6
(1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

: 139312-00-8
(1R,4S)-2-((3R,4S)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -25 - -20 ℃; for 18h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.067

Reference yield:

: 6153-06-6,105-29-3
(E)-3-methylpent-2-en-4-yn-1-ol

: 139278-51-6
(1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: sulfuric acid; water; mercury(II) oxide / 1.33 h / 60 °C

2: triethylamine / dichloromethane / 16 h / 25 °C / Inert atmosphere

3: titanium tetrachloride / dichloromethane / 18 h / -25 - -20 °C / Inert atmosphere

With sulfuric acid; water; titanium tetrachloride; triethylamine; mercury(II) oxide; In dichloromethane; 3: Diels-Alder reaction;
DOI:10.1016/j.tet.2011.09.067

Reference yield:

: 160456-56-4
(E)-5-hydroxy-3-methyl-3-penten-2-one

: 139278-51-6
(1R,4S)-2-((3S,4R)-2,4-dimethyl-1-triisopropylsiloxy-3-triisopropylsiloxymethyl-cyclohexene-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 16 h / 25 °C / Inert atmosphere

2: titanium tetrachloride / dichloromethane / 18 h / -25 - -20 °C / Inert atmosphere

With titanium tetrachloride; triethylamine; In dichloromethane; 2: Diels-Alder reaction;
DOI:10.1016/j.tet.2011.09.067