Literature DB >> 17014831

Direct epoxidation of D-glucal and D-galactal derivatives with in situ generated DMDO.

Pavel Cheshev1, Alberto Marra, Alessandro Dondoni.   

Abstract

A multi-gram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone/acetone in a biphasic system (CH(2)Cl(2)-aqueous NaHCO(3)) resulted in the formation of the corresponding 1,2-anhydrosugars in a 99% yield and 100% selectivity. In a similar way, 3,4,6-tri-O-acetyl-D-glucal afforded a 7:1 mixture of the corresponding gluco and manno derivatives in an 87% overall yield.

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Year:  2006        PMID: 17014831     DOI: 10.1016/j.carres.2006.09.003

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  8 in total

1.  Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

Authors:  Laura Alberch; Gang Cheng; Seung-Kee Seo; Xuehua Li; Fabien P Boulineau; Alexander Wei
Journal:  J Org Chem       Date:  2011-03-18       Impact factor: 4.354

2.  syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides.

Authors:  Gang Cheng; Renhua Fan; Jesús M Hernández-Torres; Fabien P Boulineau; Alexander Wei
Journal:  Org Lett       Date:  2007-10-12       Impact factor: 6.005

3.  Synthesis of Mannosidase-Stable Man3 and Man4 Glycans Containing S-linked Manα1→2Man Termini.

Authors:  Mahesh Neralkar; Leiming Tian; Richard L Redman; Isaac J Krauss
Journal:  Org Lett       Date:  2021-04-01       Impact factor: 6.005

4.  Thiacycloalkynes for copper-free click chemistry.

Authors:  Gabriela de Almeida; Ellen M Sletten; Hitomi Nakamura; Krishnan K Palaniappan; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-26       Impact factor: 15.336

5.  Synthesis and biological activity of alpha-glucosyl C24:0 and C20:2 ceramides.

Authors:  Peter J Jervis; Natacha Veerapen; Gabriel Bricard; Liam R Cox; Steven A Porcelli; Gurdyal S Besra
Journal:  Bioorg Med Chem Lett       Date:  2010-06-15       Impact factor: 2.823

6.  α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation.

Authors:  Sam J Moons; Rens A Mensink; Jeroen P J Bruekers; Maurits L A Vercammen; Laura M Jansen; Thomas J Boltje
Journal:  J Org Chem       Date:  2019-03-07       Impact factor: 4.354

7.  One-pot synthesis of glycyrrhetic acid polyglycosides based on grafting-from method using cyclic sulfite.

Authors:  Sangeetha S Shetty; Yasuhito Koyama
Journal:  Tetrahedron Lett       Date:  2016-07-02       Impact factor: 2.415

8.  Nucleotide Analogues Bearing a C2' or C3'-Stereogenic All-Carbon Quaternary Center as SARS-CoV-2 RdRp Inhibitors.

Authors:  Amarender Manchoju; Renaud Zelli; Gang Wang; Carla Eymard; Adrian Oo; Mona Nemer; Michel Prévost; Baek Kim; Yvan Guindon
Journal:  Molecules       Date:  2022-01-17       Impact factor: 4.411

  8 in total

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