Acetic acid (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-10-yl ester

Base Information

• Chemical Name: Acetic acid (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-10-yl ester
• CAS No.: 674793-08-9
• Molecular Formula: C₃₂H₃₇N₃O₉
• Molecular Weight: 607.66
• Mol file: 674793-08-9.mol

Synonyms:

Chemical Property of Acetic acid (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-10-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-10-yl ester

There total 13 articles about Acetic acid (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.0^4,8]undec-10-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:

(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 (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.04,8]undec-10-yl ester (674793-08-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 89 percent / PyHBr₃; K₂CO₃ / CH₂Cl₂

2.1: 78 percent / K₂CO₃ / methanol / 15 h / 20 °C

3.1: aq. AcOH / tetrahydrofuran / 18 h / 20 °C

4.1: pyridine / 0.17 h

5.1: 5.78 g / K₂CO₃ / methanol / 1 h / 20 °C

6.1: 85 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 7 h / 20 °C

7.1: 342 mg / DMAP; pyridine; H₂O / 33 h / 20 °C

8.1: RuCl₃*nH₂O; aq. NaIO₄ / acetonitrile; CCl₄ / 0.75 h / 20 °C

8.2: 65 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 9 h / 20 °C

9.1: 80 percent / K₂CO₃ / methanol / 0.67 h / 0 °C

10.1: HIO₄*2H₂O / various solvent(s) / 3 h / 20 °C

10.2: 41 percent / 10 h / Heating

11.1: 80 percent / DMAP; pyridine / 13 h / 20 °C

12.1: 88 percent / Na₂CO₃ / dimethylformamide / 0.25 h / Heating

13.1: 92 percent / PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.58 h / 20 °C

14.1: pyridine / 2 h / Heating

15.1: 39 mg / pyridine; Et₃N / 12 h / 20 °C

With pyridine; dmap; ruthenium trichloride; sodium periodate; disodium hydrogenphosphate; carbon tetrabromide; water; sodium carbonate; potassium carbonate; acetic acid; periodic acid; pyridinium hydrobromide perbromide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.200305111

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 (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.04,8]undec-10-yl ester (674793-08-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 78 percent / K₂CO₃ / methanol / 15 h / 20 °C

2.1: aq. AcOH / tetrahydrofuran / 18 h / 20 °C

3.1: pyridine / 0.17 h

4.1: 5.78 g / K₂CO₃ / methanol / 1 h / 20 °C

5.1: 85 percent / MCPBA; Na₂HPO₄ / CH₂Cl₂ / 7 h / 20 °C

6.1: 342 mg / DMAP; pyridine; H₂O / 33 h / 20 °C

7.1: RuCl₃*nH₂O; aq. NaIO₄ / acetonitrile; CCl₄ / 0.75 h / 20 °C

7.2: 65 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 9 h / 20 °C

8.1: 80 percent / K₂CO₃ / methanol / 0.67 h / 0 °C

9.1: HIO₄*2H₂O / various solvent(s) / 3 h / 20 °C

9.2: 41 percent / 10 h / Heating

10.1: 80 percent / DMAP; pyridine / 13 h / 20 °C

11.1: 88 percent / Na₂CO₃ / dimethylformamide / 0.25 h / Heating

12.1: 92 percent / PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.58 h / 20 °C

13.1: pyridine / 2 h / Heating

14.1: 39 mg / pyridine; Et₃N / 12 h / 20 °C

With pyridine; dmap; ruthenium trichloride; sodium periodate; disodium hydrogenphosphate; carbon tetrabromide; water; sodium carbonate; potassium carbonate; acetic acid; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.200305111

Reference yield:

Acetic acid (1R,4S,6S,7R,8S,10S,11R)-11-hydroxy-6-methoxy-11-methyl-3-oxo-8-(2,2,2-trichloro-acetylamino)-2,5-dioxa-tricyclo[5.4.0.04,8]undec-10-yl ester (674793-02-3) → Acetic acid (1R,4S,6S,7R,8S,10S,11R)-11-acetoxy-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-6-methoxy-11-methyl-3-oxo-2,5-dioxa-tricyclo[5.4.0.04,8]undec-10-yl ester (674793-08-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / DMAP; pyridine / 13 h / 20 °C

2: 88 percent / Na₂CO₃ / dimethylformamide / 0.25 h / Heating

3: 92 percent / PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.58 h / 20 °C

4: pyridine / 2 h / Heating

5: 39 mg / pyridine; Et₃N / 12 h / 20 °C

With pyridine; dmap; carbon tetrabromide; sodium carbonate; triethylamine; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200305111

upstream raw materials:

acetic anhydride

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

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

(1R,4S,5R)-5-Amino-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-5-vinyl-cyclohex-2-enol