3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate

Base Information

• Chemical Name: 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate
• CAS No.: 1192256-10-2
• Molecular Formula: C₇H₈O₃S*C₄₃H₆₃N₅O₁₁
• Molecular Weight: 998.205
• Mol file: 1192256-10-2.mol

Synonyms:

Chemical Property of 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate

There total 21 articles about 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate 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:

3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A (1056876-93-7) + toluene-4-sulfonic acid (104-15-4) → 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate (1192256-10-2)

Guidance literature:

In acetone; at 20 - 25 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm900729s

Reference yield:

3-bromo-5-methoxypyridine (50720-12-2) → 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate (1192256-10-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C

2.1: n-butyllithium / tetrahydrofuran / 1 h / -70 - -25 °C / Large scale reaction

2.2: 1 h / -70 - -65 °C

3.1: hydrogenchloride / methanol; water / 4 h / 45 °C / Large scale reaction

4.1: ferrous(II) sulfate heptahydrate; sodium 3-nitrobenzene sulfonate; sulfuric acid; boric acid / water / 6 h / 135 - 145 °C / Large scale reaction

5.1: lithium hydroxide / N,N-dimethyl-formamide / 24 h / 120 - 130 °C / Large scale reaction

6.1: sodium periodate / methanol; water / 16 h / 30 - 40 °C / Large scale reaction

7.1: lithium chloride / N,N-dimethyl-formamide / 0.5 h / 110 - 120 °C / Large scale reaction

8.1: triethylamine / tetrahydrofuran / 0.5 h / Large scale reaction

8.2: Reflux; Large scale reaction

9.1: ethyl acetate; acetonitrile / 0.5 h / 20 - 25 °C

10.1: acetone / 2 h / 20 - 25 °C / Large scale reaction

With hydrogenchloride; ferrous(II) sulfate heptahydrate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; n-butyllithium; sulfuric acid; sodium 3-nitrobenzene sulfonate; boric acid; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium chloride; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: Skraup reaction;

DOI:10.1021/op300064b

Reference yield:

tert-butyl 5-methoxy-4-methylpyridin-3-ylcarbamate (1045858-10-3) → 3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A tosylate (1192256-10-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogenchloride / methanol; water / 4 h / 45 °C / Large scale reaction

2.1: ferrous(II) sulfate heptahydrate; sodium 3-nitrobenzene sulfonate; sulfuric acid; boric acid / water / 6 h / 135 - 145 °C / Large scale reaction

3.1: lithium hydroxide / N,N-dimethyl-formamide / 24 h / 120 - 130 °C / Large scale reaction

4.1: sodium periodate / methanol; water / 16 h / 30 - 40 °C / Large scale reaction

5.1: lithium chloride / N,N-dimethyl-formamide / 0.5 h / 110 - 120 °C / Large scale reaction

6.1: triethylamine / tetrahydrofuran / 0.5 h / Large scale reaction

6.2: Reflux; Large scale reaction

7.1: ethyl acetate; acetonitrile / 0.5 h / 20 - 25 °C

8.1: acetone / 2 h / 20 - 25 °C / Large scale reaction

With hydrogenchloride; ferrous(II) sulfate heptahydrate; sodium periodate; sulfuric acid; sodium 3-nitrobenzene sulfonate; boric acid; triethylamine; lithium chloride; lithium hydroxide; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 2.1: Skraup reaction;

DOI:10.1021/op300064b

upstream raw materials:

3-descladinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-(oxycarbonyl-(1-((3-hydroxy-[1,5]naphthyridin-4-yl)-methyl)-azetidin-3-yl)-imino)-erythromycin A

toluene-4-sulfonic acid

3-bromo-5-methoxypyridine

tert-butyl 5-methoxy-4-methylpyridin-3-ylcarbamate