dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate

Base Information

• Chemical Name: dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate
• CAS No.: 1427172-59-5
• Molecular Formula: C₃₄H₃₂N₃O₁₀P
• Molecular Weight: 673.616
• Mol file: 1427172-59-5.mol

Synonyms:

Chemical Property of dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate

There total 7 articles about dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate 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: 34.0%

dibenzyl ((3-(5-bromopyridin-2-yl)-2-oxooxazolidin-5-yl)methyl) phosphate (1427172-58-4) + (3R,3aS)-3-(hydroxymethyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3a,4-dihydro-1H,3H-benzo[b]oxazolo[3,4-d][1,4]oxazin-1-one (1427171-69-4) → dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate (1427172-59-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 80 ℃; Inert atmosphere;

DOI:10.1021/jm4000598

Reference yield:

(3R,3aS)-7-bromo-3-((1,1-dimethylethyl)dimethylsilanemethyl)-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-1-one (911845-45-9) → dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate (1427172-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere

2: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; caesium carbonate; In 1,4-dioxane; water; dimethyl sulfoxide;

DOI:10.1021/jm4000598

Reference yield:

2,5-dibromopyridine (624-28-2) → dibenzyl ((3-(5-((3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)phosphate (1427172-59-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 100 °C / Inert atmosphere

2.1: N,N-dimethyl-formamide / 80 °C

3.1: methanol; potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C

4.1: 4,5-dicyano-1H-imidazole / dichloromethane / 4 h / 0 - 20 °C

4.2: 4 h / 0 - 20 °C

5.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 80 °C / Inert atmosphere

With methanol; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4,5-dicyano-1H-imidazole; potassium carbonate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm4000598

upstream raw materials:

(3R,3aS)-3-(((tert-butyldimethylsiloxy)oxy)methyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1(3H)-one

3-(5-bromopyridin-2-yl)-5-(chloromethyl)oxazolidin-2-one

(3-(5-bromopyridin-2-yl)-2-oxooxazolidin-5-yl)methyl acetate

3-(5-bromopyridin-2-yl)-5-(hydroxylmethyl)oxazolidin-2-one