154703-89-6

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 112247-51-5 S-(2'-pyridyl) 2,3-dideoxy-4,6-di-O-acetyl-1-thio-α-D-erythro-hex-2-enopyranoside 
• 2873-29-2 D-glucal triacetate 
• 90365-69-8 3,4,6-tri-O-acetyl-2-deoxy-D-arabino-hexopyranosyl bromide 
• 2873-29-2 3,4,6-tri-O-acetyl-D-glucal 

Relevant academic research and scientific papers

Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals

Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good α selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.

Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals

We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both "armed" and "disarmed" type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

A Highly Efficient Magnetic Iron(III) Nanocatalyst for Ferrier Rearrangements

A novel and highly efficient magnetic Fe 3 O 4 &at;C&at;Fe(III) core-shell catalyst, in which the carbon shell was prepared from lotus leaf, was fabricated. This nanocatalyst was successfully applied in the synthesis of a series of 2,3-unsaturated O- glycosides in excellent yields and with high selectivity, especially in the case of 2-halo O- glycosides, which differ in reactivity from nonsubstituted O- glycosides, but which have scarcely been explored before. Moreover, the catalyst could be easily separated from the reaction by the application of an external magnetic force and reused a minimum of five times without any significant decrease in the yields of the products. In addition, the reaction proceeded readily on a gram scale, which provides a bright prospect for future applications.

Palladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals

Pd(MeCN)2Cl2 enables the α-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to preactivate either donor or nucleophile. Mechanistic studies suggest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is exemplified with the synthesis of a range of glycosides and glycoconjugates of synthetic utility.

Magnetic core-shell Fe3O4@C-SO3H as an efficient and renewable 'Green catalyst' for the synthesis of O-2,3-unsaturated Glycopyra-nosides

A magnetic core-shell solid-acid catalyst Fe3O4@C-SO3H was studied for synthesis of O-2,3-unsaturated glycosides through Ferrier rearrangement. The donors include 3,4,6-tri-O-acetyl-D-glucal and 3,4-di-O-acetyl-L-rhamnal. The acceptors consist of primary alcohols, secondary alcohols, tert-butanol, unsaturated alcohols, halogenated alcohol, sterol, sugars, and phenols. O-2,3-Unsaturated glycosides were obtained rapidly (5:1 to 19:1). Moreover, the catalyst can be easily separated from the reaction with an external magnetic force and reused for a minimum of five times without any significant decrease in the yields of the products after every recycle, suggesting it a promising green catalyst in 2,3-unsaturated glycosides syntheses.

IBr-catalyzed O-glycosylation of D-glucals: Facile synthesis of 2,3-unsaturated-o-glycosides

Iodine monobromide (IBr) is explored as an alternative catalyst for the selective synthesis of 2,3-unsaturated glycosides from tri-O-acetyl-D-glucal 1 with several alcohols through Ferrier rearrangement. This reaction was shown to be a simple, efficient and cost-effective method, affords twenty examples of corresponding glycoside products in high yields with good α-selectivity.

Copper(II) triflate as a mild and efficient catalyst for ferrier glycosylation: Synthesis of 2,3-unsaturated o -glycosides

Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl-d-glucal in the presence of Cu(OTf)2 as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.

Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O-Glycosylation of 1-O-Acetyl Sugars as Glycosyl Donors

We have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2-acetoxymethylglycals with different nucleophiles, and also the O-glycosylation of 1-O-acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the O-glycosylation of 1-O-acetyl sugars gave mixtures of diastereomers with moderate to excellent selectivity.

"One-pot" access to α-d-mannopyranosides from glycals employing ruthenium catalysis

Ru-catalyzed synthesis of α-d-mannopyranosides from glucal is described via one-pot glycosylation-dihydroxylation reaction. This method is amenable to a variety of acceptors, including carbohydrate-derived and amino-acid containing alcohols to obtain mannosylated peptides and disaccharides.

Nitrosyl tetrafluoroborate catalyzed preparation of 2,3-unsaturated glycosides and 2-deoxyglycosides of hindered alcohols, thiols, and sulfonamides

Nitrosyl tetrafluoroborate (NOBF4) has been successfully applied as an efficient organocatalyst for the preparation of 2,3-unsaturated and 2-deoxyglycosides of hindered alcohols, aryl thiols, and aryl sulfonamides from glycal derivatives under