Literature DB >> 30354108

Synthesis of Glycomimetics by Diastereoselective Passerini Reaction.

Kristina Vlahoviček-Kahlina1, Mario Vazdar1, Andreja Jakas1, Vilko Smrečki2, Ivanka Jerić1.   

Abstract

We describe the utilization of bis-isopropylidene-protected d-fructose-derived aldehyde in the Passerini reaction with various acids and isocyanides. A library of densely functionalized glycomimetics bearing up to 3 carbohydrate units was obtained in high yields and diastereoselectivities. The configuration of the newly formed stereocenter was determined and the diastereoselectivity was rationalized by DFT calculations.

Entities:  

Year:  2018        PMID： 30354108     DOI： 10.1021/acs.joc.8b01874

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


  5 in total

1.  Structure and Reactivity of Glycosyl Isocyanides.

Authors:  Constantinos G Neochoritis; Ehsan Ghonchepour; Maryam Kazemi Miraki; Tryfon Zarganes-Tzitzikas; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling
Journal:  European J Org Chem       Date:  2018-11-22

2.  Synthesis of chimera oligopeptide including furanoid β-sugar amino acid derivatives with free OHs: mild but successful removal of the 1,2-O-isopropylidene from the building block.

Authors:  Kim Hoang Yen Duong; Viktória Goldschmidt Gőz; István Pintér; András Perczel
Journal:  Amino Acids       Date:  2021-02-09       Impact factor: 3.520

3.  Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi-Joullié reaction.

Authors:  Alessandro Pinna; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva; Valeria Rocca; Luca Banfi
Journal:  RSC Adv       Date:  2020-01-03       Impact factor: 3.361

Review 4.  The 100 facets of the Passerini reaction.

Authors:  Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Chem Sci       Date:  2021-09-30       Impact factor: 9.825

5.  C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction.

Authors:  Kristina Vlahoviček-Kahlina; Josipa Suć Sajko; Ivanka Jerić
Journal:  Int J Mol Sci       Date:  2019-12-10       Impact factor: 5.923
  5 in total

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