(2R)-Taxiphyllin

Base Information

• Chemical Name: (2R)-Taxiphyllin
• CAS No.: 21401-21-8
• Molecular Formula: C₁₄H₁₇NO₇
• Molecular Weight: 311.291
• Wikidata: Q105186300
• Mol file: 21401-21-8.mol

Synonyms:(2R)-Taxiphyllin;Phyllanthoside?;Phyllanthin?;SCHEMBL12727838;ZINC00895585;FT-0770936;FT-0774926;B0005-189732

Chemical Property of (2R)-Taxiphyllin

Chemical Property:

• Vapor Pressure: 1.32E-14mmHg at 25°C
• Melting Point: 137 - 140 °C (methanol)
• Boiling Point: 586.7°Cat760mmHg
• Flash Point: 308.6°C
• PSA: 143.40000
• Density: 1.56g/cm³
• LogP: -1.22662
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 311.10050188
• Heavy Atom Count: 22
• Complexity: 403

Purity/Quality:

99%, ^*data from raw suppliers

Taxiphyllin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C#N)OC2C(C(C(C(O2)CO)O)O)O)O

Technology Process of (2R)-Taxiphyllin

There total 5 articles about (2R)-Taxiphyllin 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:

methanol (67-56-1) + taxiphyllin 6'-O-gallate → methyl galloate (99-24-1) + (2R)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile (499-20-7,13115-69-0,21401-21-8)

Guidance literature:

With sodium methylate; at 20 ℃; for 4h;

DOI:10.1248/cpb.c14-00352

Reference yield:

amygdalin (29883-15-6,672-72-0) → (2R)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile (499-20-7,13115-69-0,21401-21-8)

Guidance literature:

With extracellular enzymes from Aspergillus niger; at 37 ℃; for 4h;

DOI:10.1016/j.procbio.2011.10.030

Reference yield:

4-formylphenyl acetate (878-00-2) → (2R)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile (499-20-7,13115-69-0,21401-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium perchlorate / neat (no solvent) / 0.5 h / 20 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / dichloromethane / 2 h / 20 °C / Inert atmosphere

3: trifluorormethanesulfonic acid; methanol / 3 h / 20 °C / Inert atmosphere

With methanol; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; lithium perchlorate; In dichloromethane;

DOI:10.1021/acs.jnatprod.5b01121

upstream raw materials:

amygdalin

methanol

4-formylphenyl acetate

C₁₃H₁₇NO₃Si

Refernces

• 1、 Mamdouh, Nabil Samy,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki,Kamel, Mohamed Salah. "Taxiphyllin 6′-O-gallate, actinidioionoside 6′-O-gallate and myricetrin 2′-O-sulfate from the leaves of Syzygium samarangense and their biological activities". . p. 1013 - 1018. Retrieved 2015/02/19.