28541-71-1

Basic information

• Product Name: 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside
• Synonyms: 4-Methylumbelliferyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside;4-Methylumbelliferyl tetra-O-acetyl-a-D-mannopyranoside;4-Methyl-2-oxo-2H-1-benzopyran-7-yl α-D-Mannopyranoside Tetraacetate;2H-1-Benzopyran-2-one,4-methyl-7-[(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)oxy]-
• CAS NO: 28541-71-1
• Molecular Formula: C₂₄H₂₆O₁₂
• Molecular Weight: 506.46
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives;Fluorescent Labels & Indicators
• Mol File: 28541-71-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 221-223°C
• Appearance: /
• CAS DataBase Reference: 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside(28541-71-1)
• EPA Substance Registry System: 4-Methylumbelliferyl2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside(28541-71-1)

Safety Data

• Hazardous Substances Data: 28541-71-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Crystals

Uses

A protected substrate for mannosidase.

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 5980-33-6 sodium 4-methylumbelliferonate 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 

Downstream Products

• 28541-83-5 4-methylumbellifer-7-yl α-D-mannopyranoside 

Relevant articles and documents

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.