7404-35-5

Basic information

• Product Name: Tetra-O-acetyl-L-rhamnopyranose
• Synonyms: Tetra-O-acetyl-L-rhamnopyranose;1-O,2-O,3-O,4-O-Tetraacetyl-6-deoxy-α-D-glucopyranose;Nsc403477;a-D-Glucopyranose, 6-deoxy-, tetraacetate;6-Deoxy-alpha-D-glucopyranose 1,2,3,4-tetraacetate;1,2,3,4-tetra-O-acetyl-L-rhamnopyranose
• CAS NO: 7404-35-5
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.3032
• Mol File: 7404-35-5.mol

Chemical Properties

• Melting Point: 119.5℃
• Appearance: /
• Density: 1.26±0.1 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.474
• Solubility: DMSO
• CAS DataBase Reference: Tetra-O-acetyl-L-rhamnopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: Tetra-O-acetyl-L-rhamnopyranose(7404-35-5)
• EPA Substance Registry System: Tetra-O-acetyl-L-rhamnopyranose(7404-35-5)

Safety Data

• Hazardous Substances Data: 7404-35-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tetra-O-acetyl-L-rhamnopyranose is used as a key intermediate in the synthesis of complex carbohydrates and glycosides for pharmaceutical applications. Its ability to modify the biological activity of compounds makes it a valuable component in the development of new drugs and pharmaceutical products.
Used in Organic Chemistry Research:
In the field of organic chemistry, Tetra-O-acetyl-L-rhamnopyranose serves as an important building block. It is utilized in the study and synthesis of rhamnose-containing natural products, contributing to the advancement of chemical knowledge and the discovery of novel compounds with potential applications.
Used in Food Industry:
Tetra-O-acetyl-L-rhamnopyranose is used as a component in the development of food products, where its properties can enhance or modify the characteristics of certain foods, contributing to improved taste, texture, or shelf life.
Used in Cosmetics Industry:
In cosmetics, Tetra-O-acetyl-L-rhamnopyranose is employed for its potential effects on skin health and other beneficial properties. Its incorporation into cosmetic products can lead to enhanced performance and added value for consumers seeking skincare and beauty solutions.

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 
• 6546-65-2 4',5-diacetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 

Downstream Products

• 58902-47-9 p-nitrophenyl 2,3,4-tri-O-acetyl-α-L-fucopyranoside 
• 114853-37-1 methyl 2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranoside 
• 84635-54-1 methyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 210688-75-8 Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester 
• 189135-52-2 4-methoxy-3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)toluene 
• 107802-80-2 (2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran 
• 114853-38-2 methyl 1-thio-β-L-fucopyranoside 
• 75247-29-9 (2R,3S,4R,5R,6S)-2-bromo-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 153658-86-7 (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 95581-07-0 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-L-fucopyranose 
• 103285-83-2 6-N-benzoyl-9-(2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranosyl)adenine 
• 5158-64-5 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 
• 69558-02-7 ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 
• 125520-01-6 ethyl 2,3,4-tri-O-acetyl-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.

Synthesis of aryl glycosides as vir gene inducers of Agrobacterium tumefaciens

Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated. Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated.