64913-16-2

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE
• Synonyms: 1,2,3,4-Tetra-O-acetyl-α-L(?)-fucose;Tetra-O-acetyl-α-L(?)fucopyranose;-L-fucopyranose;1,2,3,4-Tetra-O-acetyl-α(2S,3S,4R,5R,6S)-6-Methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE;1,2,3,4-TETRA-O-ACETYL-ALPHA-L-FUCOPYRANOSE;1,2,3,4-tetra-O-acetyl-A-L-(-)-fucose
• CAS NO: 64913-16-2
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.3
• Product Categories: Biochemistry;Fucose;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives
• Mol File: 64913-16-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 94 °C
• Appearance: /
• Refractive Index: -120 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• Solubility: Acetone (Sparingly), Chloroform (Slightly), Dichloromethane (Sparingly)
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE(64913-16-2)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE(64913-16-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 64913-16-2(Hazardous Substances Data)

Usage

Description

1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE, also known as T279255 (CAS# 64913-16-2), is a compound that plays a significant role in organic synthesis. It is a derivative of A-L-Fucopyranose, a monosaccharide, with four acetyl groups attached to its hydroxyl groups. This modification enhances its reactivity and stability, making it a valuable intermediate in the synthesis of various complex organic molecules.

Uses

Used in Organic Synthesis:
1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE is used as a key intermediate for the synthesis of complex organic molecules, particularly in the field of carbohydrate chemistry. Its acetylated structure provides a stable and reactive platform for further chemical modifications, enabling the development of novel compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE is used as a building block for the development of new pharmaceutical compounds. Its unique structure allows for the creation of glycoconjugates, which are known to have significant biological activities. These glycoconjugates can be used as drug candidates for the treatment of various diseases, including cancer, infectious diseases, and inflammatory conditions.
Used in Material Science:
1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE is used as a component in the development of advanced materials, such as polymers and coatings. Its ability to form stable glycosidic linkages with other monosaccharides and functional groups makes it suitable for the creation of materials with specific properties, such as improved stability, biocompatibility, and responsiveness to environmental stimuli.
Used in Food Industry:
1,2,3,4-TETRA-O-ACETYL-A-L-FUCOPYRANOSE is used as a flavor enhancer and sweetener in the food industry. Its unique structure allows it to interact with taste receptors, providing a sweet taste sensation without the high caloric content of traditional sugars. This makes it an attractive alternative for low-calorie and diabetic-friendly food products.

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

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

Downstream Products

• 58902-47-9 p-nitrophenyl 2,3,4-tri-O-acetyl-α-L-fucopyranoside 
• 69558-02-7 Ethyl 2,3,4-tri-O-acetyl-1-thio-α/β-L-fucopyranoside 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 127501-41-1 ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 127061-10-3 phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 
• 190248-99-8 ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 
• 95581-07-0 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-L-fucopyranose 

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.