24332-95-4

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE
• Synonyms: L-FUCOSE TETRAACETATE;1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE;L-Galactopyranose, 6-deoxy-, tetraacetate;1,2,3,4-Tetraacetate-6-deoxy-L-galactopyranose;NSC 119108;1,2,3,4-Tetraacetate
• CAS NO: 24332-95-4
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.3
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Fluorescent Labels & Indicators
• Mol File: 24332-95-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 371.4°Cat760mmHg
• Flash Point: 160.1°C
• Appearance: /
• Density: 1.26g/cm³
• Refractive Index: 1.474
• Storage Temp.: Refrigerator
• Solubility: Acetone (Sparingly), Chloroform (Slightly), Dichloromethane (Sparingly), Methano
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE(24332-95-4)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE(24332-95-4)

Safety Data

• Hazardous Substances Data: 24332-95-4(Hazardous Substances Data)

Usage

Description

1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE is a colorless thick syrup with unique chemical properties that make it suitable for various applications in different industries.

Uses

Used in Glycomics Research:
1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE is used as a glycoproteomic probe for the fluorescent imaging of fucosylated glycans in vivo. This application is crucial in the study of glycomics, which focuses on the structure, function, and biology of carbohydrates and their interactions with proteins.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE can be used as a key intermediate in the synthesis of various fucosylated compounds, which have potential applications in drug development and therapeutics.
Used in Chemical Synthesis:
Due to its unique chemical properties, 1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE can be employed as a versatile building block in the synthesis of complex organic molecules, particularly in the field of carbohydrate chemistry.
Used in Analytical Chemistry:
1,2,3,4-TETRA-O-ACETYL-L-FUCOPYRANOSE can also be utilized as a reference compound or standard in analytical chemistry for the identification and quantification of fucosylated glycans in various samples, such as biological fluids or tissues.

InChI:InChI=1/C14H20O9/c1-6-11(20-7(2)15)12(21-8(3)16)13(22-9(4)17)14(19-6)23-10(5)18/h6,11-14H,1-5H3/t6-,11+,12-,13-,14?/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 24332-96-5 2,3,4-Tri-O-acetyl-α-L-fucopyranosyl chloride 
• 134-96-3 syringic aldehyde 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 
• 6546-65-2 4',5-diacetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone 

Downstream Products

• 58902-47-9 p-nitrophenyl 2,3,4-tri-O-acetyl-α-L-fucopyranoside 
• 210688-75-8 Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester 
• 84635-55-2 methyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 110224-78-7 methyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 
• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 95580-90-8 2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl azide 
• 95580-98-6 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 136809-99-9 phenyl 2,3,4-tri-O-acetyl-1-seleno-α-L-rhamnopyranoside 
• 4468-73-9 phenyl-2,3,4-tri-O-acetyl-α-L-rhamnopyranoside 
• 153745-67-6 phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 
• 620951-70-4 p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 791836-41-4 para-tolyl 2-O-allyl-1-thio-α-L-rhamnopyranoside 
• 791836-34-5 (2'S,3'S)-para-tolyl 3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside 

Relevant articles and documents

A straightforward access to neohesperidose from naringin by acetolysis. Comparative behaviour of some flavonoid neohesperidosides and rutinosides under acetolysis

A straightforward semisynthesis of neohesperidose was performed in three-steps with 43% overall yield starting from naringin, the main flavonoid of grapefruit. In addition, the behaviour of two pairs of flavonoid 7-O-rhamnoglucosides (neohesperidosides naringin and rhoifolin; rutinosides hesperidin and diosmin) under same acetolysis conditions was compared. Results demonstrated the crucial influence of the oxidation state of the aglycone (flavanone or flavone), and of the nature of the disaccharidic moiety on the course of the reaction.