2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

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Chemical Name:2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide
CAS No.:444680-78-8
Molecular Formula:C₁₆H₂₂Cl₃NO₅
Molecular Weight:414.713
Hs Code.:

Synonyms:2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

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Chemical Property of 2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

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Technology Process of 2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

There total 2 articles about 2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-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%

: 444680-77-7
2,2,2-Trichloro-N-[(1R,2R,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

: 444680-78-8
2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

Guidance literature:: With titanium(IV) isopropylate; In 1,2-dichloro-ethane; for 14.5h; Heating;
DOI:10.1021/ja0265153

Reference yield:

: 253674-42-9
2,2,2-Trichloro-N-[(1R,2S,6S)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

: 444680-78-8
2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 14 h

2: 90 percent / Ti(Oi-Pr)4 / 1,2-dichloro-ethane / 14.5 h / Heating

With titanium(IV) isopropylate; disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja0265153

Reference yield:

: 444680-78-8
2,2,2-Trichloro-N-[(1R,2S,5S,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide

: Acetic acid (1R,4S,6S,7R,8R,9S,10S,11S)-10,11-diacetoxy-8-benzyliminomethyleneamino-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-9-yl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: o-iodoxybenzoic acid / dimethylsulfoxide / 2.5 h / 60 °C

2.1: o-iodoxybenzoic acid / dimethylformamide / 1.5 h / 20 °C

3.1: 94 percent / pyridine / acetonitrile / -78 - -40 °C

4.1: 93 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 4 h / 20 °C

5.1: O₃ / methanol / 0.33 h / -78 °C

5.2: 88 percent / Me₂S / methanol / -78 - 20 °C

6.1: 68 percent / tetrahydrofuran / 0 - 20 °C

7.1: pyridine / 15 h / 20 °C

8.1: 2.15 g / n-Bu₄NF / methanol; tetrahydrofuran / 0.42 h / -12 °C

9.1: HF*Py / tetrahydrofuran / 24 h

10.1: 1.15 g / pyridine / 14.5 h

11.1: 65 percent / aq. NaIO₄ / RuO₂(H₂O)x / CCl₄; acetonitrile / 41.5 h

12.1: KCN / ethanol / 5.5 h / 20 °C

13.1: HIO₄(H₂O)2 / methyl acetate / 6.5 h / 20 °C

14.1: 50 mg / pTsOH / methanol / 23 h / Heating

15.1: p-TsOH; CH(OMe)3 / methanol

16.1: DMAP; pyridine / 31 h / 20 °C

17.1: 48 mg / Na₂CO₃ / dimethylformamide / Heating

18.1: 86 percent / Ph₃P; CBr₄; Et₃N / CH₂Cl₂ / 4 h / 20 °C

With pyridine; dmap; potassium cyanide; sodium periodate; disodium hydrogenphosphate; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; ozone; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trimethyl orthoformate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; ruthenium(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; acetic acid methyl ester; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0265153