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
• Article Data: 2

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

General Description

Tetra-O-acetyl-L-rhamnopyranose is a chemical compound that belongs to the group of acetylated rhamnose derivatives. It is a sugar molecule with a pyranose ring structure and four acetyl groups attached to it. Tetra-O-acetyl-L-rhamnopyranose is commonly used in the synthesis of complex carbohydrates and glycosides, as well as in the study of rhamnose-containing natural products. It is also used in the development of drugs and pharmaceutical products due to its ability to modify the biological activity of certain compounds. Tetra-O-acetyl-L-rhamnopyranose is an important building block in the field of organic chemistry and has applications in various industries, including pharmaceuticals, food, and cosmetics.

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

• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 
• 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 

Downstream Products

• 136809-99-9 phenyl 2,3,4-tri-O-acetyl-1-seleno-α-L-rhamnopyranoside 
• 3359-36-2 O-benzyl-2,3,4-tri-O-acetyl-β-L-rhamnopyranoside 
• 127061-10-3 phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 
• 210035-70-4 2,6-dimethylphenyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 167612-34-2 phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 
• 172163-93-8 4-(2',3',4'-Tri-O-acetyl-α-L-rhamnosyloxy)benzonitrile 
• 679800-20-5 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->6)]-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 189135-52-2 4-methoxy-3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)toluene 
• 210688-75-8 Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester 
• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 24332-96-5 2,3,4-Tri-O-acetyl-α-L-fucopyranosyl chloride 
• 4468-73-9 phenyl-2,3,4-tri-O-acetyl-α-L-rhamnopyranoside 
• 5158-64-5 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 
• 103285-83-2 6-N-benzoyl-9-(2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranosyl)adenine 

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.