(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

Base Information

• Chemical Name: (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
• CAS No.: 1427171-68-3
• Molecular Formula: C₂₃H₃₆BNO₆Si
• Molecular Weight: 461.438
• Mol file: 1427171-68-3.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 32.4%

(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) + bis(pinacol)diborane (73183-34-3) → (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 (1427171-68-3) + (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)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm4000598

Reference yield: 85.0%

(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 (1427171-68-3) → (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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

DOI:10.1021/jm4000598

Reference yield:

(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 (1427171-68-3) → 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: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jm4000598

upstream raw materials:

(3R,3aS)-7-bromo-3-((1,1-dimethylethyl)dimethylsilanemethyl)-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-1-one

bis(pinacol)diborane

Downstream raw materials:

(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

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

dibenzyl (((3R,3aS)-7-(6-cyanopyridin-3-yl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl) phosphate

dibenzyl (((3R,3aS)-7-(6-((S)-3-methyl-2-oxooxazolidin-5-yl)pyridin-3-yl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)phosphate