Literature DB >> 12841734

One-pot alpha-glycosylation method using Appel agents in N,N-dimethylformamide.

Yoshihiro Nishida1, Yuko Shingu, Hirofumi Dohi, Kazukiyo Kobayashi.   

Abstract

[reaction: see text] A concept for the development of practical glycosylation is presented and demonstrated by one-pot alpha-glycosylation applying Appel agents for 2-O-benzyl-1-OH hexoses in DMF. The reaction, in situ giving the equilibrium of glycosyl bromides and more reactive O-glycoside intermediates, accomplishes a near-quantitative alpha-glycosylation removing the water molecules.

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Year:  2003        PMID： 12841734     DOI： 10.1021/ol034269+

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  The 3-Deoxy Analogue of α-GalCer: Disclosing the Role of the 4-Hydroxyl Group for CD1d-Mediated NKT Cell Activation.

Authors:  Dong Jae Baek; Jeong-Hwan Seo; Chaemin Lim; Jae Hyun Kim; Doo Hyun Chung; Won-Jea Cho; Chang-Yuil Kang; Sanghee Kim
Journal:  ACS Med Chem Lett       Date:  2011-05-16       Impact factor: 4.345

Review 2.  Direct Dehydrative Glycosylation of C1-Alcohols.

Authors:  Sloane O'Neill; Jacob Rodriguez; Maciej A Walczak
Journal:  Chem Asian J       Date:  2018-10-01

3.  Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides.

Authors:  Hayley B Steber; Yashapal Singh; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2021-03-24       Impact factor: 3.876

4.  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

5.  Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols.

Authors:  Dancan K Njeri; Erik Alvarez Valenzuela; Justin R Ragains
Journal:  Org Lett       Date:  2021-10-22       Impact factor: 6.005

6.  Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols.

Authors:  Tamashree Ghosh; Abhishek Santra; Anup Kumar Misra
Journal:  Beilstein J Org Chem       Date:  2013-05-22       Impact factor: 2.883

7.  An easy α-glycosylation methodology for the synthesis and stereochemistry of mycoplasma α-glycolipid antigens.

Authors:  Yoshihiro Nishida; Yuko Shingu; Yuan Mengfei; Kazuo Fukuda; Hirofumi Dohi; Sachie Matsuda; Kazuhiro Matsuda
Journal:  Beilstein J Org Chem       Date:  2012-04-24       Impact factor: 2.883
  7 in total

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