Literature DB >> 32293636

Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.

Subbarao Yalamanchili1, Tu-Anh V Nguyen1, Nicola L B Pohl2, Clay S Bennett1.   

Abstract

An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylmethyl and tert-butyldimethylsilyl ethers. The process affords the desired target compounds in 57-74% overall yield in just 21-37 minutes of flow time. Furthermore, unlike batch conditions, the flow processes avoided the need for active cooling to prevent unwanted exotherms and required shorter reaction times.

Entities:  

Year:  2020        PMID: 32293636      PMCID: PMC7289173          DOI: 10.1039/d0ob00522c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  30 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  Green and sustainable chemical synthesis using flow microreactors.

Authors:  Jun-ichi Yoshida; Heejin Kim; Aiichiro Nagaki
Journal:  ChemSusChem       Date:  2010-11-24       Impact factor: 8.928

3.  Homogeneous Gold-Catalyzed Glycosylations in Continuous Flow.

Authors:  Stefan Matthies; D Tyler McQuade; Peter H Seeberger
Journal:  Org Lett       Date:  2015-07-10       Impact factor: 6.005

Review 4.  Towards More Efficient, Greener Syntheses through Flow Chemistry.

Authors:  Justin A M Lummiss; Peter D Morse; Rachel L Beingessner; Timothy F Jamison
Journal:  Chem Rec       Date:  2017-02-28       Impact factor: 6.771

Review 5.  Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis.

Authors:  Henok H Kinfe
Journal:  Org Biomol Chem       Date:  2019-04-24       Impact factor: 3.876

6.  Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Authors:  Subbarao Yalamanchili; Dina Lloyd; Clay S Bennett
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

7.  Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594.

Authors:  Tao Xie; Chaoying Zheng; Kuanwei Chen; Haibing He; Shuanhu Gao
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-03       Impact factor: 15.336

8.  The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions.

Authors:  Steffen Glöckner; Duc N Tran; Richard J Ingham; Sabine Fenner; Zoe E Wilson; Claudio Battilocchio; Steven V Ley
Journal:  Org Biomol Chem       Date:  2015-01-07       Impact factor: 3.876

9.  Stereoselective synthesis of L-oliose trisaccharide via iterative alkynol cycloisomerization and acid-catalyzed glycosylation.

Authors:  Frank E McDonald; Minglang Wu
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

10.  The Lewis base-catalyzed silylation of alcohols--a mechanistic analysis.

Authors:  Pascal Patschinski; Cong Zhang; Hendrik Zipse
Journal:  J Org Chem       Date:  2014-08-11       Impact factor: 4.354

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  1 in total

1.  Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks.

Authors:  Subbarao Yalamanchili; Tu-Anh Nguyen; Alexander Zsikla; Gavin Stamper; Ashley E DeYong; John Florek; Olivea Vasquez; Nicola L B Pohl; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-21       Impact factor: 16.823

  1 in total

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