Literature DB >> 18004870

Microwave-assisted organocatalytic anomerization of alpha-C-glycosylmethyl aldehydes and ketones.

Alessandro Massi1, Andrea Nuzzi, Alessandro Dondoni.   

Abstract

The use of l-proline (30 mol %) and MW irradiation (13 W) with cooling promotes in a few hours the almost quantitative anomerization of alpha-C-glycosylmethyl aldehydes into beta-isomers. An open-chain enamine-based mechanism is postulated for this transformation. The anomerization of alpha-ketones was instead achieved by the pyrrolidine/TFA couple and MW irradiation at 120 degrees C (enamine mechanism) and by DBU as Brønsted base (enolate mechanism).

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Year:  2007        PMID： 18004870     DOI： 10.1021/jo701959b

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  An organocatalytic strategy for the stereoselective synthesis of C-galactosides with fluorine at the pseudoanomeric carbon.

Authors:  Ahmad S Altiti; S Bachan; W Alrowhani; D R Mootoo
Journal:  Org Biomol Chem       Date:  2015-11-07       Impact factor: 3.876

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.

Authors:  Jessica Zayas; Marie Annoual; Jayanta Kumar Das; Quentin Felty; Walter G Gonzalez; Jaroslava Miksovska; Nima Sharifai; Akira Chiba; Stanislaw F Wnuk
Journal:  Bioconjug Chem       Date:  2015-07-02       Impact factor: 4.774

4.  Towards new cholera prophylactics and treatment: Crystal structures of bacterial enterotoxins in complex with GM1 mimics.

Authors:  Julie Elisabeth Heggelund; Alasdair Mackenzie; Tobias Martinsen; Joel Benjamin Heim; Pavel Cheshev; Anna Bernardi; Ute Krengel
Journal:  Sci Rep       Date:  2017-05-24       Impact factor: 4.379

5.  Mild Cu(OTf)2-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group.

Authors:  Wenjing Ye; Christopher M Stevens; Peng Wen; Christopher J Simmons; Weiping Tang
Journal:  J Org Chem       Date:  2020-08-05       Impact factor: 4.354

6.  Design and Synthesis of 99mTcN-Labeled Dextran-Mannose Derivatives for Sentinel Lymph Node Detection.

Authors:  Alessandra Boschi; Micòl Pasquali; Claudio Trapella; Alessandro Massi; Petra Martini; Adriano Duatti; Remo Guerrini; Vinicio Zanirato; Anna Fantinati; Erika Marzola; Melchiore Giganti; Licia Uccelli
Journal:  Pharmaceuticals (Basel)       Date:  2018-07-16
  6 in total

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