91364-06-6

Upstream product

• 120-80-9 benzene-1,2-diol 
• 604-69-3 β-D-glucose pentaacetate 
• 1092527-97-3 C₂₃H₂₈O₁₁ 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 94356-26-0 piceatannol 3'-O-β-D-glucopyranoside 
• 94356-22-6 5-[(2E)-(3,5-dihydroxyphenyl)vinyl]-2-methoxyphenyl-1-O-β-D-glucopyranoside 
• 2400-71-7 ortho-hydroxyphenyl β-D-glucopyranoside 
• 898283-47-1 1,2-Bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene 

Relevant academic research and scientific papers

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.

Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy

Scalable syntheses of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki.Heck reaction to render the desired coupled products in high overall yield.

The synthesis of novel chromogenic enzyme substrates for detection of bacterial glycosidases and their applications in diagnostic microbiology

The preparation and evaluation of chromogenic substrates for detecting bacterial glycosidase enzymes is reported. These substrates are monoglycoside derivatives of the metal chelators catechol, 2,3-dihydroxynaphthalene (DHN) and 6,7-dibromo-2,3-dihydroxyn

Carbohydrate-templated asymmetric Diels-Alder reactions of masked ortho-benzoquinones for the synthesis of chiral bicyclo-[2.2.2]oct-5-en-2-ones

(Chemical Equation Presented) A sweet addition: Asymmetric [4 + 2] cycloaddition of masked ortho-benzoquinones with various alkenols by using sugars as chiral auxiliaries (see scheme; Bn: benzyl) affords the optically pure bicyclo[2.2.2]oct-5-en-2-ones wi

Hydrolysis of toxic natural glucosides catalyzed by cyclodextrin dicyanohydrins

The hydrolysis of toxic 7-hydroxycoumarin glucosides and other aryl and alkyl glucosides, catalyzed by modified α- and β-cyclodextrin dicyanohydrins, was investigated using different UV, redox, or HPAEC detection assays. The catalyzed reactions all followed Michaelis-Menten kinetics, and an impressive rate increase of up to 7569 (kcat/kuncat) was found for the hydroxycoumarin glucoside substrate 4-MUGP. Good and moderate degrees of catalysis (kcat/kuncat) of up to 1259 were found for the natural glucosides phloridzin and skimmin. By using a newly developed catechol detection UV-assay, a weak degree of catalysis was also found for the toxic hydroxycoumarin esculin. A novel synthesized diaminomethyl β-cyclodextrin showed a weak catalysis of p-nitrophenyl β-D-glucopyranoside hydrolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

NOUVELLE SYNTHESE DE SPIRO-ORTHOESTERS D-GLUCOSIDIQUES PAR PHOTOCYCLISATION STEREOSELECTIVE D'HYDROXYALKYL-D-GLUCOSIDES

Irradiation of hydroxyalkyl glucosides in the presence of mercury(II) oxide and iodine gave glucosidic C-1-spiroorthoesters.Where the starting glycoside had CH2OH, the cyclization was regio- and stereo-specific by α-attack.The C-1-spiroorthoesters were readily available in a "one-pot synthesis" starting from glucosyl halides.