Literature DB >> 21087037

Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation.

Sneha C Ranade1, Sophon Kaeothip, Alexei V Demchenko.   

Abstract

It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in oligosaccharide synthesis.

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Year:  2010        PMID： 21087037      PMCID： PMC3005820          DOI： 10.1021/ol1023079

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


  18 in total

1.  Stereospecific 1,2-cis-glycosylation: a modified thiocyanate method.

Authors:  N K Kochetkov; E M Klimov; N N Malysheva; A V Demchenko
Journal:  Carbohydr Res       Date:  1992-07-20       Impact factor: 2.104

2.  Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides.

Authors:  Medha N Kamat; Nigam P Rath; Alexei V Demchenko
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

3.  Mechanism of chemical O-glycosylation: from early studies to recent discoveries.

Authors:  Laurel K Mydock; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2009-11-12       Impact factor: 3.876

4.  S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis.

Authors:  Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  Chemistry       Date:  2006-08-25       Impact factor: 5.236

5.  Revisiting the armed-disarmed concept rationale: s-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis.

Authors:  Medha N Kamat; Alexei V Demchenko
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

6.  On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides.

Authors:  Sophon Kaeothip; Steven J Akins; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2010-08-10       Impact factor: 2.104

7.  S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation.

Authors:  Alexei V Demchenko; Nelli N Malysheva; Cristina De Meo
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

8.  New principles for glycoside-bond formation.

Authors:  Xiangming Zhu; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 9.  Synthesis and medical applications of oligosaccharides.

Authors:  Peter H Seeberger; Daniel B Werz
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962

Review 10.  Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccines.

Authors:  Danica P Galonić; David Y Gin
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962
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  20 in total

1.  Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects.

Authors:  Xiao G Jia; Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  J Org Chem       Date:  2016-12-07       Impact factor: 4.354

2.  S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations.

Authors:  Scott J Hasty; Mithila D Bandara; Nigam P Rath; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-02-07       Impact factor: 4.354

3.  Regenerative Glycosylation.

Authors:  Yashapal Singh; Tinghua Wang; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-12-22       Impact factor: 4.354

4.  On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: application to oligosaccharide assembly.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  J Org Chem       Date:  2011-08-17       Impact factor: 4.354

5.  OFox imidates as versatile glycosyl donors for chemical glycosylation.

Authors:  Swati S Nigudkar; Tinghua Wang; Salvatore G Pistorio; Jagodige P Yasomanee; Keith J Stine; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2017-01-04       Impact factor: 3.876

6.  S-Benzimidazolyl glycosides as a platform for oligosaccharide synthesis by an active-latent strategy.

Authors:  Scott J Hasty; Matthew A Kleine; Alexei V Demchenko
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-23       Impact factor: 15.336

7.  Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.

Authors:  S J Hasty; A V Demchenko
Journal:  Chem Heterocycl Compd (N Y)       Date:  2012-04       Impact factor: 1.277

8.  Investigation of the H-bond-mediated aglycone delivery reaction in application to the synthesis of β-glucosides.

Authors:  Michael P Mannino; Jagodige P Yasomanee; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2018-09-22       Impact factor: 2.104

9.  A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

Authors:  Scott A Geringer; Yashapal Singh; Daniel J Hoard; Alexei V Demchenko
Journal:  Chemistry       Date:  2020-06-02       Impact factor: 5.236

10.  Indolylthio Glycosides As Effective Building Blocks for Chemical Glycosylation.

Authors:  Ganesh Shrestha; Matteo Panza; Yashapal Singh; Nigam P Rath; Alexei V Demchenko
Journal:  J Org Chem       Date:  2020-07-21       Impact factor: 4.354
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