134236-17-2

Upstream product

• 108-93-0 cyclohexanol 
• 2873-29-2 D-glucal triacetate 
• 90365-69-8 3,4,6-tri-O-acetyl-2-deoxy-D-arabino-hexopyranosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 2280-44-6 D-Glucose 

Downstream Products

• 569673-23-0 cyclohexyl 3-deoxy-3-N-phenylaminomethyl-α-D-talopyranoside 
• 569673-17-2 cyclohexyl α-D-lyxo-hexopyranosid-4-(2,3:5',4')-2'-phenylisoxazolidin-4-ulose 
• 447452-27-9 cyclohexyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 
• 243125-06-6 cyclohexyl 2 ,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 637034-68-5 cyclohexyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 864863-51-4 cyclohexyl 6-O-(tert-butyldimethylsilyl)-4-O-methoxycarbonyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 

Relevant academic research and scientific papers

A facile Er(OTf)3-catalyzed synthesis of 2,3-unsaturated O- and S-glycosides

Er(OTf)3 is a useful catalyst for the Ferrier rearrangement furnishing high yields of O- and S-glycosides. The transformation has wide applicability, cleaner reaction profiles, mild reaction conditions, and high stereoselectivity and the catalyst, which is also commercially available, can be recovered and reused.

Microwave-enhanced Ferrier reaction: A facile synthesis of 2,3-unsaturated-O-glycosides under solvent-free conditions

A variety of 2,3-unsaturated- O -glycosides have been prepared by the Ferrier rearrangement of acetyl protected glycals under microwave irradiation using silica gel as an acid catalyst. Environmental friendliness, high yields, and short reaction times are the key features of this method. Furthermore, the method was applicable not only to the Ferrier reaction of 3,4,6-tri- O -acetyl glucal and 3,4,6-tri- O -acetyl galactal but also to the Ferrier reaction of 3,4-di- O -acetyl arabinal. Copyright Taylor & Francis Group, LLC.

Ferric sulphate hydrate-catalyzed, microwave-assisted synthesis of 2,3-unsaturated O-glycosides via the Ferrier reaction

Fe2(SO4)3·xH2O catalyzes the Ferrier reaction of per-O-acetylated/benzylated glycals with alcohols to give 2,3-unsaturated α-glycosides in a few minutes under microwave irradiation. Copyright Taylor & Francis Group, LLC.

Exclusive formation of α-anomers in NbCl5-promoted ferrier rearrangement for the synthesis of 2,3-unsaturated glycosides

NbCl5-catalyzed reaction of primary and secondary alcohols with tri-O-lacetyl-d-glucal is described. Exclusive formation of α-anomers of eight 2,3-unsaturated glycosides (3a-h) in high yields has been observed. Among eight unsaturated glycosides (3a-h) prepared, two of them (3d,e) are new. A new mechanism of the formation of (3a-h) from tri- O-acetyl-d-glucal and an alcohol assisted by NbCl5 as a catalyst has been suggested.{A figure is presented}. α-Unsaturated Glycoside NbCl5 Tri-O-acetyl-D-glucal Ferrier Rearrangement.

Ceric(IV) ammonium nitrate-catalyzed glycosidation of glycals: A facile synthesis of 2,3-unsaturated glycosides

Glycosidation of glycals with alcohols in the presence of a catalytic amount of ceric(IV) ammonium nitrate under neutral conditions proceeds smoothly in refluxing acetonitrile to afford the corresponding 2,3-unsaturated glycosides in excellent yields.

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- And S-linked glycosides

A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.

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.

Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions

Montmorillonite K10-catalyzed glycosylation of alcohols with glycals obtained from galactose and glucose is performed efficiently using microwave irradiation with good anomeric selectivity.

Structure-based design, synthesis and antitumoral evaluation of enulosides

Enulosides, carbohydrate derivatives containing an α,β-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60?cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. 2016 Elsevier Ltd. All rights reserved.

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.