N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide

Base Information

Chemical Name:N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide
CAS No.:253674-43-0
Molecular Formula:C₂₃H₂₈Cl₃NO₅
Molecular Weight:504.838
Hs Code.:

Synonyms:N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide

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Chemical Property of N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide

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Technology Process of N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide

There total 7 articles about N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide 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: 90.0%

: 100-39-0
benzyl bromide

: 352670-24-7
2,2,2-Trichloro-N-[(1R,2S,3R,4S,6S)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-acetamide

: 253674-43-0
N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 22h;
DOI:10.1016/S0040-4020(01)00382-9

Reference yield:

: 162089-64-7
(1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide

: 253674-43-0
N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / pyridinium bromide perbromide; K₂CO₃ / CH₂Cl₂ / 1 h / 0 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 6 h / 20 °C

3: 7.92 g / p-TsOH*H₂O / H₂O; pyridine / 1.5 h / 70 °C

4: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 11 h / 20 °C

5: 71 percent / NaBH₄; CeCl₃*7H₂O / ethanol; CH₂Cl₂ / 2.5 h / 0 - 20 °C

6: 95 percent / m-chloroperbenzoic acid; Na₂HPO₄ / CH₂Cl₂ / 24 h / 20 °C

7: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 22 h / 20 °C

With sodium tetrahydroborate; disodium hydrogenphosphate; cerium(III) chloride; pyridinium hydrobromide perbromide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00382-9

Reference yield:

: 253674-40-7
2,2,2-Trichloro-N-[(1R,2S,4S,5S)-4,5-dibromo-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-1-vinyl-cyclohexyl]-acetamide

: 253674-43-0
N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 6 h / 20 °C

2: 7.92 g / p-TsOH*H₂O / H₂O; pyridine / 1.5 h / 70 °C

3: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 11 h / 20 °C

4: 71 percent / NaBH₄; CeCl₃*7H₂O / ethanol; CH₂Cl₂ / 2.5 h / 0 - 20 °C

5: 95 percent / m-chloroperbenzoic acid; Na₂HPO₄ / CH₂Cl₂ / 24 h / 20 °C

6: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 22 h / 20 °C

With sodium tetrahydroborate; disodium hydrogenphosphate; cerium(III) chloride; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00382-9