62398-09-8

Upstream product

• 108-95-2 phenol 
• 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 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 95843-67-7 2,3-Didehydro-2,3-didesoxy-α-D-erythro-(phenyl-hexosid) 
• 119366-97-1 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-(ethoxycarbonyl)acetate 
• 119434-14-9 methyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2(R,S)-acetylacetate 
• 119367-01-0 methyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2(R,S)-acetylacetate 
• 119367-00-9 3-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-3-acetylpropanone 
• 119366-99-3 3-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-3-acetylpropanone 
• 119367-02-1 methyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2(R,S)-nitroacetate 
• 119367-04-3 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate 
• 119367-03-2 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate 
• 113019-37-7 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2(R,S)-nitroacetate 
• 113019-35-5 phenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside 

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.

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

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.

FeCl3.6H2O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-Unsaturated O-and S-Glycosides

A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a handy and eco-friendly immobilized catalyst, FeCl3.6H2O/C. A series of 2,3-unsaturated O-and S-glycosides were obtained for bioassay from corresponding 3,4,6-tri-O-acetyl-D-glucal and D-galactal in good to excellent yields (56%-99%) and high anomeric selectivity (α/β = 7:1 to >19:1). Furthermore, the catalyst was efficient on gram-scale reactions and recyclable for at least three times.

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

ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides

An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl-d-glucal to 2,3-unsaturated-O-glycosides with high α-selectivity.

(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides

A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-d-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive α-stereoselectivity.

A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst

A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-d-glycal to 2,3-unsaturated O-glycosides. A wide range of alcoh

Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives

The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an α anomer with high stereoselectivity. We have found that 3-O-mesyl-d-glycals 2-4 were smoothly reacted with alcohols in th