(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol

Base Information

• Chemical Name: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol
• CAS No.: 914922-79-5
• Molecular Formula: C₂₆H₃₅BO₁₁
• Molecular Weight: 534.368
• Mol file: 914922-79-5.mol

Synonyms:(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol

Chemical Property of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol

There total 9 articles about (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol 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: 92.0%

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-chlorobenzene (135700-53-7) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol (914922-79-5)

Guidance literature:

With potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; In diethylene glycol dimethyl ether; at 165 ℃; for 20h; Product distribution / selectivity;

Reference yield: 72.0%

(2R,3R,4R,5S,6S)-2-[(acetyloxy)methyl]-6-(4-bromophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (852204-49-0) + bis(pinacol)diborane (73183-34-3) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol (914922-79-5)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 88 ℃; for 2.91667h; Product distribution / selectivity;

Reference yield:

(1S)-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol (914922-78-4) + acetic anhydride (108-24-7) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol (914922-79-5)

Guidance literature:

With pyridine; In tetrahydrofuran; at 50 ℃; for 12h; Product distribution / selectivity;

upstream raw materials:

(2R,3R,4R,5S,6S)-2-[(acetyloxy)methyl]-6-(4-bromophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

bis(pinacol)diborane

(1S)-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol

acetic anhydride

Downstream raw materials:

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(3'-(benzyloxy)-4'-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-azetidin-2-yl}biphenyl-4-yl)-D-glucitol

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(3'-(benzyloxy)-4'-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-4-yl)-D-glucitol