67945-53-3

Usage

Uses

Used in Organic Synthesis:
4-Methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is used as a synthetic intermediate for the preparation of complex organic molecules and pharmaceuticals. Its unique structure allows for the selective functionalization and modification of the molecule, making it a useful building block in the synthesis of various compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is used as a key component in the development of new drugs and therapeutic agents. Its unique properties and reactivity enable the creation of novel drug candidates with potential applications in various therapeutic areas.
Used in Research and Development:
4-Methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is also used in research and development settings to study the properties and reactivity of complex organic molecules. Its unique structure provides a platform for understanding the behavior of similar compounds and contributes to the advancement of organic chemistry and related fields.

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

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 604-69-3 β-D-glucose pentaacetate 
• 84380-11-0 7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran tetrabutylammonium salt 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 

Downstream Products

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 17833-43-1 4-methyl-umbelliferyl α-D-glucopyranoside 

Relevant academic research and scientific papers

Concise synthesis of sulfoquinovose and sulfoquinovosyl diacylglycerides, and development of a fluorogenic substrate for sulfoquinovosidases

The sulfolipid sulfoquinovosyl diacylglycerol (SQDG) and its headgroup, the sulfosugar sulfoquinovose (SQ), are estimated to harbour up to half of all organosulfur in the biosphere. SQ is liberated from SQDG and related glycosides by the action of sulfoquinovosidases (SQases). We report a 10-step synthesis of SQDG that we apply to the preparation of saturated and unsaturated lipoforms. We also report an expeditious synthesis of SQ and (13C6)SQ, and X-ray crystal structures of sodium and potassium salts of SQ. Finally, we report the synthesis of a fluorogenic SQase substrate, methylumbelliferyl α-d-sulfoquinovoside, and examination of its cleavage kinetics by two recombinant SQases. These compounds will assist in dissecting the role of sulfoglycolysis in the biogeochemical sulfur cycle and understanding the molecular basis of sulfoglycolysis.

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.