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

Base Information

• Chemical Name: Acetic acid (1R,4S,6R,7R,8R,9S,10S,11S)-10,11-diacetoxy-8-(3-benzyl-ureido)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-9-yl ester
• CAS No.: 444681-02-1
• Molecular Formula: C₂₅H₃₀N₂O₁₁
• Molecular Weight: 534.52

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

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

Chemical Property:

Purity/Quality:

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

There total 18 articles about Acetic acid (1R,4S,6R,7R,8R,9S,10S,11S)-10,11-diacetoxy-8-(3-benzyl-ureido)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-9-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:

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 (253674-42-9) → Acetic acid (1R,4S,6R,7R,8R,9S,10S,11S)-10,11-diacetoxy-8-(3-benzyl-ureido)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.04,8]undec-9-yl ester (444681-02-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 96 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 14 h

2.1: 90 percent / Ti(Oi-Pr)4 / 1,2-dichloro-ethane / 14.5 h / Heating

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

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

5.1: 94 percent / pyridine / acetonitrile / -78 - -40 °C

6.1: 93 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 4 h / 20 °C

7.1: O₃ / methanol / 0.33 h / -78 °C

7.2: 88 percent / Me₂S / methanol / -78 - 20 °C

8.1: 68 percent / tetrahydrofuran / 0 - 20 °C

9.1: pyridine / 15 h / 20 °C

10.1: 2.15 g / n-Bu₄NF / methanol; tetrahydrofuran / 0.42 h / -12 °C

11.1: HF*Py / tetrahydrofuran / 24 h

12.1: 1.15 g / pyridine / 14.5 h

13.1: 65 percent / aq. NaIO₄ / RuO₂(H₂O)x / CCl₄; acetonitrile / 41.5 h

14.1: KCN / ethanol / 5.5 h / 20 °C

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

16.1: 50 mg / pTsOH / methanol / 23 h / Heating

17.1: DMAP; pyridine

18.1: Na₂CO₃ / dimethylformamide / Heating

With pyridine; titanium(IV) isopropylate; dmap; potassium cyanide; sodium periodate; disodium hydrogenphosphate; tetrabutyl ammonium fluoride; sodium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; ozone; periodic acid; 3-chloro-benzenecarboperoxoic acid; 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; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0265153

Reference yield:

2,2,2-Trichloro-N-[(1R,2S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-5,6-dioxo-1-vinyl-cyclohex-3-enyl]-acetamide (1026684-08-1) → Acetic acid (1R,4S,6R,7R,8R,9S,10S,11S)-10,11-diacetoxy-8-(3-benzyl-ureido)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.04,8]undec-9-yl ester (444681-02-1)

Guidance literature:

Multi-step reaction with 15 steps

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

2.1: 94 percent / pyridine / acetonitrile / -78 - -40 °C

3.1: 93 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 4 h / 20 °C

4.1: O₃ / methanol / 0.33 h / -78 °C

4.2: 88 percent / Me₂S / methanol / -78 - 20 °C

5.1: 68 percent / tetrahydrofuran / 0 - 20 °C

6.1: pyridine / 15 h / 20 °C

7.1: 2.15 g / n-Bu₄NF / methanol; tetrahydrofuran / 0.42 h / -12 °C

8.1: HF*Py / tetrahydrofuran / 24 h

9.1: 1.15 g / pyridine / 14.5 h

10.1: 65 percent / aq. NaIO₄ / RuO₂(H₂O)x / CCl₄; acetonitrile / 41.5 h

11.1: KCN / ethanol / 5.5 h / 20 °C

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

13.1: 50 mg / pTsOH / methanol / 23 h / Heating

14.1: DMAP; pyridine

15.1: Na₂CO₃ / dimethylformamide / Heating

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

DOI:10.1021/ja0265153

Reference yield:

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 (444680-77-7) → Acetic acid (1R,4S,6R,7R,8R,9S,10S,11S)-10,11-diacetoxy-8-(3-benzyl-ureido)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.04,8]undec-9-yl ester (444681-02-1)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 90 percent / Ti(Oi-Pr)4 / 1,2-dichloro-ethane / 14.5 h / Heating

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

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

4.1: 94 percent / pyridine / acetonitrile / -78 - -40 °C

5.1: 93 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 4 h / 20 °C

6.1: O₃ / methanol / 0.33 h / -78 °C

6.2: 88 percent / Me₂S / methanol / -78 - 20 °C

7.1: 68 percent / tetrahydrofuran / 0 - 20 °C

8.1: pyridine / 15 h / 20 °C

9.1: 2.15 g / n-Bu₄NF / methanol; tetrahydrofuran / 0.42 h / -12 °C

10.1: HF*Py / tetrahydrofuran / 24 h

11.1: 1.15 g / pyridine / 14.5 h

12.1: 65 percent / aq. NaIO₄ / RuO₂(H₂O)x / CCl₄; acetonitrile / 41.5 h

13.1: KCN / ethanol / 5.5 h / 20 °C

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

15.1: 50 mg / pTsOH / methanol / 23 h / Heating

16.1: DMAP; pyridine

17.1: Na₂CO₃ / dimethylformamide / Heating

With pyridine; titanium(IV) isopropylate; dmap; potassium cyanide; sodium periodate; disodium hydrogenphosphate; tetrabutyl ammonium fluoride; sodium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; ozone; periodic acid; 3-chloro-benzenecarboperoxoic acid; 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; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0265153

upstream raw materials:

benzylamine

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

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

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

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