(2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 105330-58-3
• Molecular Formula: C₂₄H₃₀O₁₁
• Molecular Weight: 494.496
• Mol file: 105330-58-3.mol

Synonyms:

Chemical Property of (2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

There total 1 articles about (2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 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:

(+)-catechin 3'-O-β-D-glucopyranoside (105330-51-6) + dimethyl sulfate (77-78-1) → (2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (105330-58-3)

Guidance literature:

With potassium carbonate; In acetone; for 2.5h; Heating;

DOI:10.1248/cpb.34.3208

Reference yield:

(2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (105330-58-3) → 5,7,4'-tri-O-methyl-(+)-catechin diacetate (105330-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 9 mg / dimethylsulfoxide; H₂O / 37 °C / hesperidinase

2: 6 mg / pyridine / 2 h / Ambient temperature

With pyridine; In water; dimethyl sulfoxide;

DOI:10.1248/cpb.34.3208

Reference yield:

(2S,3R,4S,5S,6R)-2-[5-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (105330-58-3) → (+)-catechin 6-C-β-D-glucopyranoside (105371-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfoxide; H₂O / 37 °C / hesperidinase

2: 23 mg / p-toluenesulfonic acid / dioxane / 10 h / 80 °C

With toluene-4-sulfonic acid; In 1,4-dioxane; water; dimethyl sulfoxide;

DOI:10.1248/cpb.34.3208

upstream raw materials:

(+)-catechin 3'-O-β-D-glucopyranoside

dimethyl sulfate

Downstream raw materials:

D-glucose

(2R,3S)-5,7-dimethoxy-2-(3'-hydroxy-4'-methoxyphenyl)chroman-3-ol

5,7,4'-tri-O-methyl-(+)-catechin diacetate

(+)-catechin 6-C-β-D-glucopyranoside

Refernces