3.12 Carbohydrate Derived Auxiliaries: Mono (and Disaccharide) Derivatives

The chemistry of 2‐C‐formyl‐glycals has witnessed tremendous growth over the last two decades. Functionalized compounds derived from 2‐C‐formyl‐glycals have found applications in organic synthesis, carbohydrate chemistry, medicinal chemistry, supramolecular chemistry, and materials chemistry. These advancements can be mainly attributed to the availability of a very simple and general procedure for the direct formylation of glycals by using the Vilsmeier–Haack reaction. The highly conjugated α,β‐unsaturated carbonyl functional group present in 2‐C‐formyl‐glycals provides opportunities for synthetic elaboration, which can lead to a variety of natural and unnatural compounds for varied applications. This review summarizes the recent developments in the synthesis and applications of these versatile chiral intermediates.

show abstract

2‐Nitroglycals: Versatile Building Blocks for the Synthesis of 2‐Aminoglycosides

Delaunay

Poisson

Jubault

et al. 2014

Eur J Org Chem

View full text Add to dashboard Cite

Abstract2‐Deoxy‐2‐amino‐substituted glycosides are ubiquitous compounds in biochemistry and biology. Therefore, the development of new synthetic pathways to access natural and non‐natural derivatives is highly desirable. In that context, 2‐nitroglycals appeared as versatile building blocks for reaching those targets. Since their first introduction almost forty years ago, their synthetic utility has been widely demonstrated and they have been used to access natural and non‐natural compounds with potent biological activity. The aim of this review is to summarize the developed routes to these versatile intermediates as well as their reactivity. The main applications of the chemistry developed with 2‐nitroglycal derivatives is also highlighted in this first review.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

3.12 Carbohydrate Derived Auxiliaries: Mono (and Disaccharide) Derivatives

Cited by 3 publications

References 396 publications

ChemInform Abstract: Carbohydrate‐Derived Auxiliaries: Mono (and Disaccharide) Derivatives

ChemInform Abstract: Carbohydrate‐Derived Auxiliaries: Mono (and Disaccharide) Derivatives

Applications of 2‐C‐Formyl‐Glycals in Organic Synthesis

2‐Nitroglycals: Versatile Building Blocks for the Synthesis of 2‐Aminoglycosides

Contact Info

Product

Resources

About