56650-22-7

Basic information

• Product Name: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Synonyms: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 56650-22-7
• Molecular Weight: 486.56
• Mol File: 56650-22-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(56650-22-7)
• EPA Substance Registry System: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(56650-22-7)

Safety Data

• Hazardous Substances Data: 56650-22-7(Hazardous Substances Data)

Upstream product

• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 2216-51-5 (-)-menthol 
• 108-24-7 acetic anhydride 
• 604-69-3 β-D-glucose pentaacetate 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 100432-86-8 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 16203-27-3 (-)-menthyl β-D-glucopyranoside 

Relevant articles and documents

Solvent-Free Glycosylation from per-O-Acylated Donors Catalyzed by Methanesulfonic Acid

The huge importance of carbohydrates and their derivatives in biomedical and industrial applications call for the development of streamlined and sustainable procedures for their synthetic elaboration. Here reported a novel glycosylation method based on direct activation of readily available per-O-acylated (acetylated or benzoylated) donors, promoted under air by methanesulfonic acid as a cheap and green catalyst in the absence of any solvent. Besides the beneficial avoidance of toxic and polluting organic solvents, these conditions were found critical for activating such poorly reactive donors with a very small catalyst loading (only 5 mol %), instead of stoichiometric Lewis acid promoters typically employed. Desired glycosides were quickly obtained, in most cases with high 1,2-trans stereoselectivity. Other main advantages over reported glycosylations with similar donors are the limited stoichiometric excess of the acceptor (or the donor), the easy applicability and low cost of the procedure and the wide target scope, also covering the synthesis of disaccharides and other non-trivial glycosides with applicable potential.

Sulfonated graphene oxide as highly efficient catalyst for glycosylation

Heterogeneous sulfonated graphene oxide for the first time has been used as a green and efficient catalyst for atom-economic glycosylation of unprotected, unactivated glycosyl donors or 2,3,4,6-tetra-O-acetylglycosyltrichloroacetimidate with various accep

Solvent-free mechanochemical glycosylation in ball mill

Starting from acetobromosugars and an alcohol (alkyl/substituted alkyl/akenyl/alkynyl/glyceryl/cyclohexyl/steryl) various O-glycosides have been prepared mechanochemically under solvent-free conditions employing a planetary ball mill in the presence of metal carbonates (environmentally benign or otherwise) as promoters. The method was proven to be mild and efficient and applicable on preparative scale for the synthesis of various mono- and disaccharide glycosides. 4-Pentenyl glycoside so produced could, in four successive reactions in the same pot, be converted in high isolated yields into triazole-substituted pentyl glycoside that can find application in the area of medicinal chemistry.