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Jamison, T. F. et al.: 2018 Science of Synthesis, 2018/5: Flow Chemistry in Organic Synthesis DOI: 10.1055/sos-SD-228-00279
Flow Chemistry in Organic Synthesis

13 The Controlled Synthesis of Carbohydrates

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Book

Editors: Jamison, T. F.; Koch, G.

Authors: Beeler, A. B.; Beingessner, R. L.; Bottecchia, C.; Browne, D. L.; Coley, C. W.; Ferguson, S.; Folgueiras-Amador, A. A.; Gilmore, K.; Hicklin, R. W.; Imbrogno, J.; Itsuno, S.; Jamison, T. F.; Jensen, K. F.; Kelly, L. P.; Kerr, M. S.; Kiesman, W. F.; Kim, H.; Kwok, D.-I. A.; Ley, S. V.; Longstreet, A. R.; May, S. A. ; McTeague, T. A.; Mijalis, A. J.; Mo, Y.; Moon, S.; Myerson, A.; Noël, T.; O’Brien, A. G.; O’Brien, M.; O’Mahony, M.; Opalka, S. M.; Pentelute, B. L.; Polyzos, A. ; Schepartz, A.; Seeberger, P. H.; Seo, H.; Steinauer, A.; Stelzer, T.; Stephenson, C. R. J.; Strom, A. E.; Styduhar, E. D.; Sun, A. C.; Telmesani, R.; Thomas, D. A.; Tran, T. H.; Ullah, M. S.; Wicker, A. C.; Wirth, T.; Yoshida, J.

Title: Flow Chemistry in Organic Synthesis

Print ISBN: 9783132423312; Online ISBN: 9783132423350; Book DOI: 10.1055/b-006-161272

1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner (Editor-in-Chief), A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

While the formation of the glycosidic bond is the key transformation in the synthesis of polysaccharides, a dominant class of biopolymer, the reaction is poorly understood and remains highly challenging to perform reliably and selectively in a laboratory setting. This is due to the numerous intermediates and competing mechanistic pathways present, all of which are extremely sensitive to the environmental conditions of the reaction. This sensitivity and irreproducibility is an excellent opportunity to take advantage of the inherent control over reaction conditions achievable in micro- and meso-flow reactors. In this chapter, the range of transformations performed under continuous-flow conditions related to the synthesis of carbohydrates, including glycosidic bond formation, functional-group manipulations, and multistep synthesis, are presented and discussed. The advantages gained in flow are highlighted and, where available, directly compared to the respective batch process.

Key words

Keywords: - carbohydrates - flow chemistry - mixing - multistep - stereoselective - glycosylation - glycosidic bond - micromixer - microfluidic - monosaccharide - oligosaccharide - polysaccharide - automation - solid-phase synthesis
 
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