CID 9981176

Base Information

• Chemical Name: CID 9981176
• CAS No.: 54081-48-0
• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.399
• DSSTox Substance ID: DTXSID201019949
• Nikkaji Number: J665.434G
• Wikidata: Q105382133
• Mol file: 54081-48-0.mol

Synonyms:(2R-cis)-isomer of astilbin;(2S-cis)-isomer of astilbin;3-0-alpha-1-rhamnosyl-(2R,3R)-dihydroquercetin;astilbin;isoastilbin;neoisoastilbin

Chemical Property of CID 9981176

Chemical Property:

• Melting Point: 278-280 °C (decomp)
• Boiling Point: 801.1±65.0 °C(Predicted)
• PKA: 7.34±0.60(Predicted)
• PSA: 186.37000
• Density: 1.74±0.1 g/cm3(Predicted)
• LogP: 0.03810
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 450.11621151
• Heavy Atom Count: 32
• Complexity: 676

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Isoastilbin(NewProduct) 98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@H](OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O

Technology Process of CID 9981176

There total 8 articles about CID 9981176 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: 91.0%

(2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one (294203-79-5) → astilbin (29838-67-3,54081-47-9,54081-48-0,54141-72-9)

Guidance literature:

With hydrogen; palladium; In methanol;

DOI:10.1016/S0040-4039(00)00826-1

Reference yield:

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → astilbin (29838-67-3,54081-47-9,54081-48-0,54141-72-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂ / 2 h / -78 - -35 °C

2: 66 percent / DDQ; H₂O / CH₂Cl₂ / 5 h / 25 °C

3: 85 percent / pyridinium dichromate / CH₂Cl₂ / 40 h / 20 °C

4: 91 percent / H₂ / Pd black / methanol / 50 h / 25 °C

With dipyridinium dichromate; bis(cyclopentadienyl)hafnium dichloride; water; hydrogen; silver perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.08.076

Reference yield:

1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose (80152-99-4) → astilbin (29838-67-3,54081-47-9,54081-48-0,54141-72-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂ / 2 h / -78 - -35 °C

2: 66 percent / DDQ; H₂O / CH₂Cl₂ / 5 h / 25 °C

3: 85 percent / pyridinium dichromate / CH₂Cl₂ / 40 h / 20 °C

4: 91 percent / H₂ / Pd black / methanol / 50 h / 25 °C

With dipyridinium dichromate; bis(cyclopentadienyl)hafnium dichloride; water; hydrogen; silver perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.08.076

upstream raw materials:

astilbin

(2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one

1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose

2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride

Downstream raw materials:

(2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-α-L-rhamnopyranosyloxy-chroman-4-one

(2R)-5,7-diacetoxy-2r-(3,4-diacetoxy-phenyl)-3t-(tri-O-acetyl-α-L-rhamnopyranosyloxy)-chroman-4-one

(2S,3R)-dihydroquercetin 3-O-α-L-rhamnoside

(+/-)-taxifolin

Refernces

• 1、 -. "PROCESS FOR PREPARING FLAVONOIDS". Example 6. . Retrieved 2008/06/13.