Piceoside Tetraacetate

Base Information

• Chemical Name: Piceoside Tetraacetate
• CAS No.: 25876-45-3
• Molecular Formula: C22H26O11
• Molecular Weight: 466.442
• Mol file: 25876-45-3.mol

Synonyms:4-Acetylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside;1-[4-[(2,3,4,6-Tetra-O-acetyl--D-glucopyranosyl)oxy]phenyl]ethanone;Picein Tetraacetate;

Chemical Property of Piceoside Tetraacetate

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 171-173 °C
• Refractive Index: 1.528
• Boiling Point: 552.658 °C at 760 mmHg
• Flash Point: 237.098 °C
• PSA: 140.73000
• Density: 1.31 g/cm³
• LogP: 1.35110
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

4-Acetylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Piceoside Tetraacetate

There total 7 articles about Piceoside Tetraacetate 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: 90.0%

acetyl chloride (75-36-5) + phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4468-72-8) → p-hydroxyacetophenone-4-O-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranoside (25876-45-3)

Guidance literature:

With trifluorormethanesulfonic acid; at 0 ℃; for 0.166667h;

DOI:10.3987/COM-08-S(F)39

Reference yield: 90.0%

acetyl chloride (75-36-5) + phenyl-β-D-glucopyranoside (1464-44-4) → p-hydroxyacetophenone-4-O-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranoside (25876-45-3) + phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4468-72-8)

Guidance literature:

With trifluorormethanesulfonic acid; at 0 ℃; for 0.166667h;

DOI:10.3987/COM-08-S(F)39

Reference yield: 42.0%

4-Hydroxyacetophenone (99-93-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → p-hydroxyacetophenone-4-O-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranoside (25876-45-3)

Guidance literature:

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In chloroform; water; Heating;

DOI:10.1023/A:1013971214679

upstream raw materials:

4-Hydroxyacetophenone

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

2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose

acetic anhydride

Downstream raw materials:

3-Morpholin-4-yl-1-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propan-1-one; hydrochloride

3-Piperidin-1-yl-1-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propan-1-one; hydrochloride

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-(4-acetyl-phenoxy)-6-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-(4-acetyl-phenoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Refernces

• 1、 Al Bittar, Sheiraz,Mora, Nathalie,Loonis, Michèle,Dangles, Olivier. "A simple synthesis of 3-deoxyanthocyanidins and their O-glucosides". . p. 4294 - 4302. Retrieved 2016/07/06.
• 2、 Pavlov,Sokolov,Zakharov. "Structure and reactivity of glycosides: IV. Koenigs-Knorr synthesis of aryl β-D-glucopyranosides using phase-transfer catalysts". . p. 1811 - 1814. Retrieved 2007/10/03.