25876-45-3

Basic information

• Product Name: Piceoside Tetraacetate
• Synonyms: 1-[4-[(2,3,4,6-Tetra-O-acetyl--D-glucopyranosyl)oxy]phenyl]ethanone;4-Acetylphenyl 2,3,4,6-Tetra-O-acetyl--D-glucopyranoside;Picein Tetraacetate;Piceoside Tetraacetate;4-Acetylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside
• CAS NO: 25876-45-3
• Molecular Formula: C₂₂H₂₆O₁₁
• Molecular Weight: 466.44
• Product Categories: Carbohydrates & Derivatives;Glucuronides
• Mol File: 25876-45-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 171-173 °C
• Boiling Point: 552.658 °C at 760 mmHg
• Flash Point: 237.098 °C
• Appearance: Yellow solid
• Density: 1.31 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.528
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: Piceoside Tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Piceoside Tetraacetate(25876-45-3)
• EPA Substance Registry System: Piceoside Tetraacetate(25876-45-3)

Safety Data

• Hazardous Substances Data: 25876-45-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C22H26O11/c1-11(23)16-6-8-17(9-7-16)32-22-21(31-15(5)27)20(30-14(4)26)19(29-13(3)25)18(33-22)10-28-12(2)24/h6-9,18-22H,10H2,1-5H3/t18?,19-,20?,21?,22-/m1/s1

Upstream product

• 99-93-4 4-Hydroxyacetophenone 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 4468-72-8 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 149104-90-5 4-acetylphenylboronic acid 

Downstream Products

• 530-14-3 picein 
• 159185-42-9 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-(4-acetyl-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3-yl ester 
• 159185-41-8 1-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-ethanone 
• 159185-40-7 Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-(4-acetyl-phenoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 159185-43-0 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 
• 132767-56-7 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 
• 132767-57-8 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 

Relevant articles and documents

Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature

Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.

Effective friedel-crafts acylations of O- and C-arylglycosides with triflic acid

Triflic acid is well known not only as a Friedel-Crafts promoter, but also as a deglycosidation reagent. In this study, we promote effective Friedel-Crafts acylations for O- or C-arylglucosides without deglycosidation and check their inhibitory activities for β-glucosidase.

Phenolic and triterpenoid glycosides from Aster batangensis

A new phenolic glycoside, asterbatanoside A [p-hydroxyacetophenone-4-O-β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside], and two new triterpenoid saponins, asterbatanoside B [2α,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside] and asterbatanoside C [3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28- oicacid-28-O-β-D-glucopyranoside] were isolated from the roots of Aster batangensis. Their structures were determined by spectroscopic methods and chemical evidence. The total synthesis of asterbatanoside A is also reported. Copyright