(3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate

Base Information

• Chemical Name: (3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate
• CAS No.: 102475-76-3
• Molecular Formula: C₂₂H₂₆O₁₀
• Molecular Weight: 450.442
• Mol file: 102475-76-3.mol

Synonyms:(3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property of (3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate

There total 2 articles about (3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate 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:

4-Iodoacetophenone (13329-40-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate + (3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate (102475-76-3)

Guidance literature:

With dmap; nickel(II) perchlorate hexahydrate; hydrogen bromide; acetic acid; magnesium chloride; zinc; In tetrahydrofuran; at 0 ℃; for 12h; Overall yield = 70 %; Overall yield = 47.2 mg; stereoselective reaction; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03567

Reference yield:

Acetyl bromide (506-96-7) + (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene (13231-13-5) → (3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate (102475-76-3)

Guidance literature:

With aluminium trichloride; Petroleum ether;

upstream raw materials:

Acetyl bromide

(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene

4-Iodoacetophenone

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide