(1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

Base Information

Chemical Name:(1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one
CAS No.:497075-40-8
Molecular Formula:C₂₇H₃₃NO₅
Molecular Weight:451.563
Hs Code.:

Synonyms:(1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

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Chemical Property of (1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

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Technology Process of (1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

There total 3 articles about (1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-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:

: 502897-36-1
(1R,5R)-5,8,8-Trimethyl-2-oxo-3-oxa-bicyclo[3.2.1]octane-1-carbonyl chloride

: 497075-40-8
(1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent Spectr_. / CD₂Cl₂ / 1 h / 20 °C

2: 1.298 g / trimethylsilyl triflate / CH₂Cl₂; tetrahydrofuran / 3 h / -78 °C

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; dichloromethane-d2;
DOI:10.1016/S0040-4020(02)00675-0

Reference yield:

: 183850-84-2
5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carboxylic acid

: 497075-40-8
(1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / 3 h

2: 83 percent Spectr_. / CD₂Cl₂ / 1 h / 20 °C

3: 1.298 g / trimethylsilyl triflate / CH₂Cl₂; tetrahydrofuran / 3 h / -78 °C

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; dichloromethane-d2;
DOI:10.1016/S0040-4020(02)00675-0

Reference yield:

: 37610-80-3
1,3-dioxolan-2-ylethylmagnesium bromide

: 4-phenyl-1-[(1S,5R)-5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]oct-1-ylcarbonyl]pyridinium trifluoromethanesulfonate

: (1S,5R)-1-[(2R)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

: 497075-40-8
(1S,5R)-1-[(2S)-2-(2-[1,3]dioxolan-2-ylethyl)-4-phenyl-1,2-dihydropyridyl-1-carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at -78 ℃; for 3h;
DOI:10.1016/S0040-4020(02)00675-0