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

Base Information

• Chemical Name: 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
• CAS No.: 253674-49-6
• Molecular Formula: C₂₅H₃₀Cl₃NO₁₀
• Molecular Weight: 610.873

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 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

There total 17 articles about 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 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: 100.0%

acetic anhydride (108-24-7) + (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 (352670-32-7) → 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 (253674-49-6)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 24h;

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

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)-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 (253674-49-6)

Guidance literature:

Multi-step reaction with 15 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

13.1: H₅IO₆ / ethyl acetate / 24 h / 20 °C

14.1: 772 mg / DL-camphorsulfonic acid / methanol / 10 h / 20 °C

15.1: 100 percent / 4-dimethylaminopyridine / pyridine / 24 h / 20 °C

With dmap; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; cerium(III) chloride; camphor-10-sulfonic acid; 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; periodic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; 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)-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 (253674-49-6)

Guidance literature:

Multi-step reaction with 14 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

12.1: H₅IO₆ / ethyl acetate / 24 h / 20 °C

13.1: 772 mg / DL-camphorsulfonic acid / methanol / 10 h / 20 °C

14.1: 100 percent / 4-dimethylaminopyridine / pyridine / 24 h / 20 °C

With dmap; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; cerium(III) chloride; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

acetic anhydride

(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

benzyl bromide

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

Downstream raw materials:

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,6R,7S,8R,9S,10S)-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-9-benzyloxy-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-5-(3-benzyl-ureido)-6-dimethoxymethyl-8-methyl-3-oxo-2-oxa-bicyclo[3.3.1]non-4-yl ester

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