[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate
• CAS No.: 103292-13-3
• Molecular Formula: C₂₁H₂₄O₁₂
• Molecular Weight: 468.414
• Mol file: 103292-13-3.mol

Synonyms:[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate

Chemical Property of [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate

There total 2 articles about [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate 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: 80.0%

2,4-Dihydroxybenzaldehyde (95-01-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate (103292-13-3)

Guidance literature:

With Tris(3,6-dioxaheptyl)amine; potassium chloride; sodium hydrogencarbonate; In dichloromethane; for 48h; Reflux;

DOI:10.1016/j.dyepig.2012.07.006

Reference yield: 32.0%

2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (19186-59-5) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 4-Formyl-3-hydroxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (103292-13-3,103292-20-2,142393-08-6)

Guidance literature:

With sodium hydroxide; In water; acetone; for 15h; Ambient temperature;

DOI:10.1016/0008-6215(86)85043-1

Reference yield: 95.0%

2-(Aminomethyl)pyridine (3731-51-9) + [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-3-hydroxyphenoxy)oxan-2-yl]methyl acetate (103292-13-3) → 5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2-{[(2-methylpyridinyl)-E-imino]methylphenol}

Guidance literature:

In ethanol; for 4 - 6h;

DOI:10.1039/c6dt04615k

upstream raw materials:

2,4-Dihydroxybenzaldehyde

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

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

Downstream raw materials:

2-methoxy-4-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]benzaldehyde

4-Formyl-3-methoxyphenyl β-D-glucopyranoside

3-Methoxy-4-(2-nitrovinyl)phenyl β-D-glucopyranoside

5-[2-hydroxy-4-((2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy)benzylidene]-barbituric acid