(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1453855-58-7
• Molecular Formula: C₂₆H₃₅BO₁₁
• Molecular Weight: 534.368
• Mol file: 1453855-58-7.mol

Synonyms:(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 5 articles about (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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:

[(2R,3R,4R,5R,6R)-3,4,5-triacetoxy-6-(3-bromophenyl)tetrahydropyran-2-yl]methyl acetate (1453855-56-5) + bis(pinacol)diborane (73183-34-3) → (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1453855-58-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 60 ℃; for 22h; Inert atmosphere;

Reference yield:

(3-bromophenyl)boronic acid (89598-96-9) → (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1453855-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium diacetate / acetonitrile / 23 h / 20 °C / Inert atmosphere

2: 4-methylmorpholine N-oxide; methanesulfonamide; osmium(VIII) oxide; 2,6-dimethylpyridine / water; tert-butyl alcohol; tetrahydrofuran / 72 h / 20 °C

3: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C

4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 22 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; osmium(VIII) oxide; methanesulfonamide; potassium acetate; palladium diacetate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

D-glucal triacetate (2873-29-2) → (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1453855-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium diacetate / acetonitrile / 23 h / 20 °C / Inert atmosphere

2: 4-methylmorpholine N-oxide; methanesulfonamide; osmium(VIII) oxide; 2,6-dimethylpyridine / water; tert-butyl alcohol; tetrahydrofuran / 72 h / 20 °C

3: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C

4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 22 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; osmium(VIII) oxide; methanesulfonamide; potassium acetate; palladium diacetate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

upstream raw materials:

(3-bromophenyl)boronic acid

((2R,3S,6S)-3-acetoxy-6-(3-bromophenyl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

((2R,3S,4R,5S,6R)-3-acetoxy-6-(3-bromophenyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl acetate

D-glucal triacetate

Downstream raw materials:

(2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-[3-[4-(5-methyloxazol-2-yl)phenyl]phenyl]tetrahydropyran-3,4,5-triol

(2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-[3-[3-hydroxy-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]phenyl]tetrahydropyran-3,4,5-triol

N-methyl-3-[[3-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]phenyl]methyl]benzamide

C₂₃H₂₃NO₅