2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose
• CAS No.: 914922-76-2
• Molecular Formula: C₄₀H₃₉BrO₅
• Molecular Weight: 679.651
• Mol file: 914922-76-2.mol

Synonyms:2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose

Chemical Property of 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose

There total 5 articles about 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose 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: 77.0%

(2,3,4,6-tetra-O-benzyl-2-β-D-glucopyranosyl)tri-n-butylstannane + bis(4-bromophenyl)iodonium triflate (139139-81-4) → 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose (914922-76-2)

Guidance literature:

With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(3,5-bis(trifluoromethyl)phenyl)(2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1’-biphenyl]-2-yl)phosphine; copper(l) chloride; In 1,4-dioxane; at 110 ℃; for 72h; stereospecific reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00475

Reference yield:

1,4-bromoiodobenzene (589-87-7) → N-(5-(4-bromophenyl)pent-4-yn-1-yl)-4-methylbenzenesulfonamide + 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose (914922-76-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 100 ℃; for 12h;

DOI:10.1038/s41557-018-0078-8

Reference yield:

1,4-bromoiodobenzene (589-87-7) → N-(5-(4-bromophenyl)pent-4-yn-1-yl)-4-methylbenzenesulfonamide + 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-bromophenyl)-β-D-glucopyranose (914922-76-2) + 1-bromo-4-(4-methoxy-3-methylbut-3-en-1-yl)benzene + 1-bromo-4-(4-methoxy-3-methylbut-3-en-1-yl)benzene

Guidance literature:

1,4-bromoiodobenzene; N-(but-3-yn-1-yl)-4-methylbenzenesulfonamide; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20 ℃; for 2h;

1-Bromo-2-phenylacetylene; With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; In toluene; at 80 ℃; for 5h;

DOI:10.1002/cjoc.201800437

upstream raw materials:

1,4-bromoiodobenzene

bis(4-bromophenyl)iodonium triflate

1.4-dibromobenzene

Downstream raw materials:

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