67909-25-5

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)-
• Synonyms: 2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)-;(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 67909-25-5
• Molecular Formula: C₂₄H₂₆O₁₂
• Molecular Weight: 506.456
• Product Categories: Carbohydrates & Derivatives
• Mol File: 67909-25-5.mol

Chemical Properties

• Boiling Point: 607.8°Cat760mmHg
• Flash Point: 259.6°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 1.02E-14mmHg at 25°C
• Refractive Index: 1.555
• Solubility: Dichloromethane, Methanol
• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)-(67909-25-5)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)-(67909-25-5)

Safety Data

• Hazardous Substances Data: 67909-25-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of diverse chemical entities through reactions such as acylation, alkylation, and glycosylation. This makes it a valuable building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)is utilized as a starting material for the synthesis of novel drug candidates. Its ability to form a wide range of derivatives makes it a promising candidate for the development of new therapeutic agents with improved pharmacological properties.
Used in Agrochemical Industry:
2H-1-Benzopyran-2-one, 4-methyl-7-((2,3,4,6-tetra-O-acetyl-beta-D-gluc opyranosyl)oxy)also finds applications in the agrochemical industry, where it serves as a precursor for the synthesis of new pesticides and plant growth regulators. Its unique structural features enable the development of innovative agrochemicals with enhanced efficacy and selectivity.

InChI:InChI=1/C24H26O12/c1-11-8-20(29)35-18-9-16(6-7-17(11)18)34-24-23(33-15(5)28)22(32-14(4)27)21(31-13(3)26)19(36-24)10-30-12(2)25/h6-9,19,21-24H,10H2,1-5H3/t19-,21-,22+,23-,24-/m1/s1

Upstream product

• 83-87-4 D-glucose pentaacetate 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 4336-91-8 3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-68-2 α-D-glucopyranose peracetylate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 172364-20-4 4-methylumbelliferyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>3)-2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside 
• 172364-19-1 4-methylumbelliferyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>3)-2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside 
• 172364-23-7 7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one 
• 172364-16-8 4-methylumbelliferyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 172364-12-4 4-methylumbelliferyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 18997-57-4 4-methylumbelliferyl β-D-glucopyranoside 

Relevant articles and documents

Based on 4 - methyl [...] synthesis method of a plurality of glycoside

The invention discloses a method for synthesizing various glucosides on a basis of 4-methylumbelliferone. According to the invention, a glycosyl donor peracetyl saccharide and a glycosyl acceptor 4-methylumbelliferone are subjected to a glycosylation reaction under room temperature or under heating with dichloromethane or 1,2-dichloroethane as a solvent and with the combined effect of Lewis acid boron trifluoride ethyl ether and organic alkali triethylamine or pyridine; and protecting groups are removed, such that various glucosides based on 4-methylumbelliferone can be obtained. The glucosides include 4-methylumbelliferone-beta-D-glucopyranosiduronide, 4-methylumbelliferone-beta-D-glucopyranoside, 4-methylumbelliferone-beta-D-xylopyranoside, 4-methylumbelliferone-beta-D-ribofuranoside, 4-methylumbelliferone-alpha-D-galactopyranoside, and 4-methylumbelliferone-alpha-D-mannopyranoside. The method is simple, and can produce a beta or alpha single-configuration target. A glycosylation reaction yield can reach 17-93%.

Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides

Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2-cis glycopyranosides is reported, as exemplified by aryl α-d-galacto-, α-d-gluco- and 2-azido α-d-glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.

An improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms

An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogenic 4-methylumbelliferyl glycoside substrates. Due to the use of base, the glycosylation reaction proceeds more easily, is uncommonly α- or β-stereoselective, and affords the corresponding products in moderate to excellent yields (51%-94%) under appropriate conditions.

Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors

A series of 7-substituted coumarins incorporating various glycosyl moieties were synthesized and investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). These coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II, but some of them inhibited tumor-associated CA IX and XII in the low nanomolar range. They also significantly inhibited the growth of primary tumors by the highly aggressive 4T1 syngeneic mouse mammary tumor cells at 30 mg/kg, constituting interesting candidates for the development of conceptually novel anticancer drugs. Because CA IX is overexpressed in hypoxic tumors and exhibits very limited expression in normal tissues, such compounds may be useful for treating cancers not responsive to classic chemo- and radiotherapy.

Synthesis of 4-methylumbelliferyl-β-D-glucan oligosaccharides as specific chromophoric substrates of (1 -> 3),(1 -> 4)-β-D-glucan 4-glucanohydrolases

Keywords: β-D-Glucan oligosaccharides; 4-Methylumbelliferyl glycosides; β-Glucanase substrates; NMR data