3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl beta-D-allopyranoside

Base Information

• Chemical Name: 3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl beta-D-allopyranoside
• CAS No.: 20565-42-8
• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.4
• Mol file: 20565-42-8.mol

Synonyms:

Chemical Property of 3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl beta-D-allopyranoside

Chemical Property:

• Vapor Pressure: 4.64E-25mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl beta-D-allopyranoside

There total 8 articles about 3,5-dihydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl beta-D-allopyranoside 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: 80.7%

UDP-glucose (133-89-1) + 2',4',6',4-tetrahydroxydihydrochalcone (25515-46-2,73692-50-9) → chalconaringenin 2'-glucoside (20565-42-8,26107-98-2,28757-26-8) + C21H22O10

Guidance literature:

With C-glycosyltransferase from Mangifera indica; In methanol; at 40 ℃; for 12h; pH=6.6; Enzymatic reaction;

DOI:10.1002/chem.201600411

Reference yield: 40.8%

4-O-Benzoylphloracetophenone 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside) (130471-79-3) → 2,4,4',6-Tetrahydroxychalcone 2'-O-α-D-mannopyranoside (4547-85-7,72843-28-8,114612-67-8,121545-97-9,130549-92-7,138665-97-1,20565-42-8,26107-98-2,28757-26-8)

Guidance literature:

With potassium hydroxide; In ethanol; Ambient temperature;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → 2,4,4',6-Tetrahydroxychalcone 2'-O-α-D-mannopyranoside (4547-85-7,72843-28-8,114612-67-8,121545-97-9,130549-92-7,138665-97-1,20565-42-8,26107-98-2,28757-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 29.2 percent / mercuric cyanide / nitromethane / Heating

2: 40.8 percent / 60 percent aq. KOH / ethanol / Ambient temperature

With potassium hydroxide; mercury(II) cyanide; In nitromethane; ethanol;

upstream raw materials:

naringenin-5-O-glucoside

4-hydroxy-benzaldehyde

UDP-glucose

2',4',6',4-tetrahydroxydihydrochalcone

Downstream raw materials:

naringenin-5-O-glucoside

Refernces

• 1、 Esaki, Sachiko,Abe, Manami,Shiba, Naoko,Kamiya, Shintaro. "Synthesis of Glycyphyllin". . p. 1583 - 1585. Retrieved 2007/10/02.