A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH2X2 derived C1-building blocks-Reference-Cited by-同舟云学术

A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH₂X₂ derived C₁-building blocks

Published:2023 Issue:36 Volume:14 Page:9838-9842
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Kirupakaran Sujenth¹,Arago Glib¹^ORCID,Hirschhäuser Christoph¹^ORCID

Affiliation:

1. University of Duisburg-Essen, Universitätsstr. 5-7, 45117 Essen, Germany

Abstract

The synthesis of aldohexoses from CH2X2 derived C1-building blocks relies on Matteson homologation and strategically applied, boron mediated olefinations. A 25 min video tutorial is available via QR-code or this link: https://youtu.be/vXy5oVavJUU.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/SC/D3SC03778A

Reference76 articles.

1. A.Varki and J. B.Lowe , Essentials of Glycobiology , ed. A. Varki , Cold Spring Harbor Laboratory Press , Cold Spring Harbour, NewYork , 2nd edn, 2009 , p. 80

2. Protein-glycan interactions in the control of innate and adaptive immune responses

3. The repertoire of glycan determinants in the human glycome

4. Recent developments of ionic liquids in oligosaccharide synthesis: the sweet side of ionic liquids

5. “Cap-Tag”—Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis Financial support from the donors of the Petroleum Research Fund, administered by the ACS (ACS-PRF 34649-G1), Merck (Predoctoral Fellowship for E.R.P.), Boehringer-Ingelheim (Predoctoral Fellowship for E.R.P.), and the NIH (Biotechnology Training Grant for M.C.H.) is gratefully acknowledged. Funding for the MIT-DCIF Inova 501 was provided by the NSF (Award CHE-9808061). Funding for the MIT-DCIF Avance (DPX) 400 was provided by the NIH (Award 1S10RR13886-01). We thank Silicycle (Quebec City, Canada) for the generous gift of fluorous silica gel and isocyanate silica gel scavenger resin. We thank Dr. O. Plante for helpful discussions and help with the automated oligosaccharide synthesizer.

Cited by 1 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Differentially Protected Glycols from α‐Halo Boronic Esters and Lithiated Benzoates;European Journal of Organic Chemistry;2023-12-13