24332-98-7

Basic information

• Product Name: METHYL BETA-L-FUCOPYRANOSIDE
• Synonyms: METHYL BETA-L-FUCOPYRANOSE;METHYL BETA-L-FUCOPYRANOSIDE;methyl-6-deoxy-B-L-galactopyranoside;.beta.-L-Galactopyranoside, methyl 6-deoxy-;Methylb-L-fucopyranoside;METHYL-SS-L-FUCOPYRANOSIDE;Methyl 6-deoxy-β-L-galactopyranoside;(2S,3S,4R,5S,6S)
• CAS NO: 24332-98-7
• Molecular Formula: C₇H₁₄O₅
• Molecular Weight: 178.18
• Product Categories: Biochemistry;Fucose;Glycosides;Sugars
• Mol File: 24332-98-7.mol
• Article Data: 51

Chemical Properties

• Melting Point: 123 °C
• Boiling Point: 312.6oC at 760 mmHg
• Flash Point: 142.9oC
• Appearance: /
• Density: 1.32g/cm3
• Vapor Pressure: 4.59E-05mmHg at 25°C
• Refractive Index: 1.513
• PKA: 13.05±0.70(Predicted)
• CAS DataBase Reference: METHYL BETA-L-FUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL BETA-L-FUCOPYRANOSIDE(24332-98-7)
• EPA Substance Registry System: METHYL BETA-L-FUCOPYRANOSIDE(24332-98-7)

Safety Data

• Hazardous Substances Data: 24332-98-7(Hazardous Substances Data)

Usage

General Description

Methyl Beta-L-Fucopyranoside is a chemical compound that belongs to the family of fucose sugars. It is a methylated form of Beta-L-Fucopyranoside, which is a type of sugar molecule commonly found in biological organisms. Methyl Beta-L-Fucopyranoside is often used in research and industrial applications as a chemical building block for the synthesis of various complex carbohydrate molecules. It has also shown potential biological activities, including anti-inflammatory and anti-tumor effects. Additionally, it has been studied for its potential application in drug delivery systems and as a component of glycosylation reactions in the pharmaceutical industry.

InChI:InChI=1/C7H14O5/c1-3-4(8)5(9)6(10)7(11-2)12-3/h3-10H,1-2H3/t3-,4+,5+,6-,7-/m0/s1

Upstream product

• 67-56-1 methanol 
• 2438-80-4 L-Fucose 
• 7647-01-0 hydrogenchloride 
• 6752-75-6 methyl-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-altropyranoside 
• 73139-31-8 methyl-2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-desoxy-α-D-altropyranoside 
• 6340-57-4 methyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranoside 
• 53942-13-5 Methyl 2,3,4-Tri-O-acetyl-6-deoxy-β-D-galactopyranoside 
• 73-34-7 D-Fucose 
• 121043-13-8 merremoside c 
• 121043-12-7 merremoside a 
• 3615-41-6 L-Rhamnose 
• 96048-23-6 methyl-2-O-α-L-rhamnopyranosyl-β-D-fucopyranoside 
• 150650-49-0 methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-D-galactopyranoside 
• 111476-43-8 methyl β-D-glucopyranoside 6-phenylthionocarbonate 

Downstream Products

• 14064-39-2 L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal 
• 3615-37-0 D-Fucose 
• 134311-92-5 methyl-2,4-di-O-benzyl-β-D-quinovopyranoside 
• 176380-03-3 methyl 2,3‐di‐O‐benzyl‐6‐deoxy‐β‐D‐glucopyranoside 
• 197657-27-5 methyl-2-O-benzyl-β-D-quinovopyranoside 
• 51288-33-6 C₂₁H₂₂O₇ 
• 51236-57-8 C₂₁H₂₂O₇ 
• 15830-76-9 methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-talopyranoside 
• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 1379777-16-8 methyl 3-O-phenoxythiocarbonyl-β-L-fucopyranoside 
• 1128-40-1 methyl 6-deoxy-β-L-glucopyranoside 
• 134645-97-9 methyl 2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranoside 
• 87171-57-1 methyl 2,3,4-tri-O-(p-bromobenzoyl)-β-L-fucopyranoside 

Relevant articles and documents

Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation

A Cu(II)-catalyzed diastereoselective Michael/aldol cascade approach is used to accomplish concise total syntheses of cardiotonic steroids with varying degrees of oxygenation including cardenolides ouabagenin, sarmentologenin, 19-hydroxysarmentogenin, and 5-epi-panogenin. These syntheses enabled the subsequent structure activity relationship (SAR) studies on 37 synthetic and natural steroids to elucidate the effect of oxygenation, stereochemistry, C3-glycosylation, and C17-heterocyclic ring. Based on this parallel evaluation of synthetic and natural steroids and their derivatives, glycosylated steroids cannogenol-l-α-rhamnoside (79a), strophanthidol-l-α-rhamnoside (92), and digitoxigenin-l-α-rhamnoside (97) were identified as the most potent steroids demonstrating broad anticancer activity at 10-100 nM concentrations and selectivity (nontoxic at 3 μM against NIH-3T3, MEF, and developing fish embryos). Further analyses indicate that these molecules show a general mode of anticancer activity involving DNA-damage upregulation that subsequently induces apoptosis.

Synthesis of Deoxyglycosides by Desulfurization under UV Light

This study was performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite is also discussed.

Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions

A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA]+Br3-) accelerates the regioselective oxidation at the axial -OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.