76223-29-5

Upstream product

• 150-76-5 4-methoxy-phenol 
• 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 

Downstream Products

• 1310542-97-2 C₁₈H₂₂O₆ 
• 1310542-89-2 C₁₃H₁₄O₅ 
• 197449-45-9 p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside 
• 197449-49-3 p-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-α-D-allopyranoside 
• 197449-42-6 p-methoxyphenyl 6-O-acetyl-2,3,4-trideoxy-2-trichloroacetamido-α-D-erythro-hex-3-enopyranoside 
• 197449-38-0 p-methoxyphenyl 6-O-acetyl-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-α-D-erythro-hex-2-enopyranoside 
• 197449-50-6 p-methoxyphenyl α-N-acetyl-D-allosaminide 
• 197449-37-9 p-methoxyphenyl 6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 197449-36-8 p-methoxyphenyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 149342-25-6 ((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate 

Relevant academic research and scientific papers

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.

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.

Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement

By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.

ZnBr2-catalyzed and microwave-assisted synthesis of 2,3-unsaturated glucosides of hindered phenols and alcohols

GRAPHICAL ABSTRACT Zinc bromide (ZnBr2) under microwave irradiation efficiently catalyzed the Ferrier reaction of hindered phenols and alcohols to afford the corresponding α-2,3-unsaturated glucoside acetates in good yields and with good stereoselectivity. The reaction affords a facile access to new 2,3-dideoxyglucosides of important phenolic and alcoholic constituents of spices.

Sm(OTf)3as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals

By using Sm(OTf)3as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal or 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in g

Aluminium triflate catalysed O-glycosidation: Temperature-switched selective Ferrier rearrangement or direct addition with alcohols

A temperature-controlled mechanism switch between the Al(OTf) 3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the st

2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercula

Reactions of various nucleophiles with d-glucal over keggin-type heteropoly compounds: A simple, rapid, and expedient method for the synthesis of pseudoglycals

The reaction of benzyl alcohol with 3,4,6-tri-O-acetyl-d-glucal has been investigated with several heteropoly compounds, and the optimal catalyst is 12-tungstophosphoric acid supported on carbon. In the presence of this catalyst, various alcohols gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields and good anomeric selectivity under solvent-free condition. 4,6-Di-O-acetyl-2,3-dideoxy - d-erythro-hex-2- enopyranosyl cyanide and ethyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio - d-erythro-hex-2-enopyranoside have also been prepared with trimethylsilyl cyanide and ethanthiol as nucleophiles, respectively. The catalyst could be easily recovered and reused several times with slight loss of activity. The selectivity to give α-anomers predominantly did not show any change in all runs.

Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-D-galactal: Mild, eco-friendly, rapid glycosidation with allylic rearrangement

Montmorillonite K10 was found to catalyze, under microwave irradiation, rapid O-glycosidation of 3,4,6-tri-O-acetyl-D-galactal to afford exclusively the alkyl and aryl 2,3-dideoxy-D-threo-hex-2-enopyranosides with very high α-selectivity and without the formation of the 2-deoxy-D-lyxo-hexopyranosides. Under these conditions, 3,4,6-tri-O-acetyl-D-glucal as usual also underwent the Ferrier rearrangement.

Highly stereoselective synthesis of pseudoglycals via Yb(OTf)3 catalyzed Ferrier glycosylation

The reaction of tri-O-acetyl-D-glucal with various alcohols and thiols was effectively promoted by a catalytic amount of Yb(OTf)3 to produce a variety of pseudoglycals via Ferrier rearrangement in excellent yields and anomeric selectivity.