N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide

Base Information

Chemical Name:N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide
CAS No.:1421851-05-9
Molecular Formula:C₂₁H₂₆Cl₃NO₅
Molecular Weight:478.8
Hs Code.:

Synonyms:N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide

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Chemical Property of N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide

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Technology Process of N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide

There total 5 articles about N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide 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: 91.0%

: 1421851-04-8
2,2,2-trichloro-N-((1R,2S,3R,6S)-4-(dimethoxymethyl)-2-hydroxy-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)acetamide

: 100-39-0
benzyl bromide

: 1421851-05-9
N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide

Guidance literature:: 2,2,2-trichloro-N-((1R,2S,3R,6S)-4-(dimethoxymethyl)-2-hydroxy-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)acetamide; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; N,N-dimethyl-formamide; for 10h;
DOI:10.1021/jo302773f

Reference yield:

: C₁₂H₁₂Cl₃NO₃

: 1421851-05-9
N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: CSA / methanol / 1 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

3.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 30 h / 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

4.2: 10 h

With disodium hydrogenphosphate; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo302773f

Reference yield:

: 271256-59-8
2,2,2-Trichloro-N-[(1R,6S)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-2-oxo-1-vinyl-cyclohex-3-enyl]-acetamide

: 1421851-05-9
N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: periodic acid dihydrate / ethyl acetate / 4 h / 20 °C / Inert atmosphere

2.1: CSA / methanol / 1 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

4.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 30 h / 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

5.2: 10 h

With disodium hydrogenphosphate; periodic acid dihydrate; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo302773f