Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester

Base Information

• Chemical Name: Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester
• CAS No.: 253674-37-2
• Molecular Formula: C₂₅H₃₀Cl₃NO₉
• Molecular Weight: 594.874

Synonyms:Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester

Chemical Property of Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester

There total 14 articles about Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester 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: 75.0%

Acetic acid (R)-1-[(1R,2S,3S,4S,6S)-2-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-(2,2,2-trichloro-acetylamino)-7-oxa-bicyclo[4.1.0]hept-3-yl]-prop-2-ynyl ester (253674-46-3) → Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester (253674-37-2)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; acetonitrile; at 20 ℃; for 4.5h;

DOI:10.1002/(SICI)1521-3773(19991018)38:20<3081::AID-ANIE3081>3.0.CO;2-6

Reference yield:

(1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide (162089-64-7) → Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester (253674-37-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / pyridinium bromide perbromide; K₂CO₃ / CH₂Cl₂ / 1 h / 0 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 6 h / 20 °C

3.1: 7.92 g / p-TsOH*H₂O / H₂O; pyridine / 1.5 h / 70 °C

4.1: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 11 h / 20 °C

5.1: 71 percent / NaBH₄; CeCl₃*7H₂O / ethanol; CH₂Cl₂ / 2.5 h / 0 - 20 °C

6.1: 95 percent / m-chloroperbenzoic acid; Na₂HPO₄ / CH₂Cl₂ / 24 h / 20 °C

7.1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 22 h / 20 °C

8.1: O₃ / methanol / 1.17 h / -78 °C

8.2: 96 percent / Me₂S / methanol / -78 - 20 °C

9.1: EtMgBr / tetrahydrofuran; diethyl ether / 0.58 h / 0 - 20 °C

9.2: tetrahydrofuran; diethyl ether / 2 h / 20 °C

10.1: n-Bu₄NF / tetrahydrofuran / 2.5 h / 20 °C

11.1: 7.37 g / pyridine / 5.5 h

12.1: 75 percent / RuO₂(H₂O)x; NaIO₄ / acetonitrile; CCl₄; H₂O / 4.5 h / 20 °C

With ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; cerium(III) chloride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; pyridinium hydrobromide perbromide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)00382-9

Reference yield:

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 (253674-40-7) → Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester (253674-37-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 6 h / 20 °C

2.1: 7.92 g / p-TsOH*H₂O / H₂O; pyridine / 1.5 h / 70 °C

3.1: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 11 h / 20 °C

4.1: 71 percent / NaBH₄; CeCl₃*7H₂O / ethanol; CH₂Cl₂ / 2.5 h / 0 - 20 °C

5.1: 95 percent / m-chloroperbenzoic acid; Na₂HPO₄ / CH₂Cl₂ / 24 h / 20 °C

6.1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 22 h / 20 °C

7.1: O₃ / methanol / 1.17 h / -78 °C

7.2: 96 percent / Me₂S / methanol / -78 - 20 °C

8.1: EtMgBr / tetrahydrofuran; diethyl ether / 0.58 h / 0 - 20 °C

8.2: tetrahydrofuran; diethyl ether / 2 h / 20 °C

9.1: n-Bu₄NF / tetrahydrofuran / 2.5 h / 20 °C

10.1: 7.37 g / pyridine / 5.5 h

11.1: 75 percent / RuO₂(H₂O)x; NaIO₄ / acetonitrile; CCl₄; H₂O / 4.5 h / 20 °C

With ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; cerium(III) chloride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)00382-9

upstream raw materials:

Acetic acid (R)-1-[(1R,2S,3S,4S,6S)-2-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-(2,2,2-trichloro-acetylamino)-7-oxa-bicyclo[4.1.0]hept-3-yl]-prop-2-ynyl ester

benzyl bromide

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

(3aR,4S,7aS)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methyl-2-trichloromethyl-3a-vinyl-3a,4,5,7a-tetrahydro-benzooxazole

Downstream raw materials:

(1S,4S,5R,6S,8S,9S)-9-(benzyloxy)-6-(dimethoxymethyl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloroacetamido)-2-oxabicyclo[3.3.1]nonan-4-yl acetate

Acetic acid (1S,4S,6R,7S,8R,9S,10S)-9-benzyloxy-8-(3-benzyl-ureido)-6-methoxy-10-methyl-3-oxo-2,5-dioxa-tricyclo[5.2.2.0^4,8]undec-10-yl ester

Acetic acid (1S,4S,5R,6S,8S,9S)-8-acetoxy-9-benzyloxy-6-dimethoxymethyl-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester

Acetic acid (1S,4S,5R,6S,8S,9S)-8-acetoxy-9-benzyloxy-5-(3-benzyl-ureido)-6-dimethoxymethyl-8-methyl-3-oxo-2-oxa-bicyclo[3.3.1]non-4-yl ester

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