6160-79-8

Basic information

• Product Name: 4-Methylumbelliferyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside
• Synonyms: 4-Methylumbelliferyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside;4-Methyl-7-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-2H-1-benzopyran-2-one;7-(β-D-Galactopyranosyloxy)-4-Methyl-couMarin Tetraacetate
• CAS NO: 6160-79-8
• Molecular Formula: C₂₄H₂₆O₁₂
• Molecular Weight: 506.45604
• Product Categories: Carbohydrates & Derivatives;Fluorescent Labels & Indicators
• Mol File: 6160-79-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 607.8°C at 760 mmHg
• Flash Point: 259.6°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 1.02E-14mmHg at 25°C
• Refractive Index: 1.555
• Solubility: Chloroform,
• CAS DataBase Reference: 4-Methylumbelliferyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylumbelliferyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside(6160-79-8)
• EPA Substance Registry System: 4-Methylumbelliferyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside(6160-79-8)

Safety Data

• Hazardous Substances Data: 6160-79-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Protected substrate for fluorometric assay of ?-D-galactosidase.

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

• 4163-60-4 β-D-galactose peracetate 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 572-09-8 acetobromogalactose 
• 108-46-3 recorcinol 
• 25878-60-8 D-galactose pentaacetate 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 281207-18-9 2-(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyloxy)-1,3,2-dioxaphosphinane 2-oxide 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 6160-78-7 4-methylumbelliferyl-β-D-galactopyranoside 
• 296776-06-2 4-methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside 
• 296776-03-9 4-methylumbelliferyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 
• 296776-04-0 4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside 

Relevant articles and documents

A 4-methyl umbrella-type keto -β-D method for preparing-galactopyranoside

The invention discloses a preparation method of 4-methyl umbrella-shaped keto-beta-D-pyran galactoside. The method comprises the following steps: step 1, preparing 4-methyl umbrella-shaped ketone; step 2, preparing tetra acetyl-Alpha-D-pyran galactoside; step 3, preparing 4-methyl umbrella-shaped keto-2,3,4,6-tetra acetyl-beta-D-pyran galactoside; and step 4, preparing the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside. The method is moderate in reaction condition, namely, the reactions are carried out at a room temperature; heavy metallic salts are not required, so that the environmental friendliness is realized; the yield is high, namely, the one-step yield of glycosylations can reach 73.1% and the total yield of the glycosylations can rach 32.9%. The microbiology experiment proves that the effects of the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside are equal to the effects of an imported substrate, so that the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside can be used for replacing an imported product.

Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions

We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methylimidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6- trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl) imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the β isomer regardless of neighboring group effects.