scholarly journals Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot

2017 ◽  
Vol 15 (3) ◽  
pp. 559-563 ◽  
Author(s):  
Mithila D. Bandara ◽  
Jagodige P. Yasomanee ◽  
Nigam P. Rath ◽  
Christian M. Pedersen ◽  
Mikael Bols ◽  
...  
Keyword(s):  
Building Blocks ◽  
Oligosaccharide Synthesis ◽  
One Pot ◽  
Glycosyl Donors

A new series of superarmed glycosyl donors has been investigated.

scholarly journals Extending the S-benzimidazolyl (SBiz) platform: N-alkylated SBiz glycosyl donors with the universal activation profile

2017 ◽  
Vol 89 (9) ◽  
pp. 1321-1331
Author(s):  
Scott J. Hasty ◽  
Nigam P. Rath ◽  
Alexei V. Demchenko
Keyword(s):  
Lewis Acid ◽  
Building Blocks ◽  
Oligosaccharide Synthesis ◽  
Activation Profile ◽  
Chemical Glycosylation ◽  
High Yields ◽  
Activation Conditions ◽  
Glucose Pentaacetate ◽  
Glycosyl Donors

AbstractThis article describes the development of alkylated S-benzimidazolyl (SBiz) imidates as versatile building blocks for chemical glycosylation. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations and its utility was further extended to other common strategies for oligosaccharide synthesis. This article expands upon the utility of these compounds. We developed a general protocol for the synthesis of a series of N-alkylated SBiz glycosides from N-protected SBiz aglycones by Lewis acid-mediated coupling with glucose pentaacetate. The N-alkylated SBiz moiety was found to be stable under strong basic conditions which allowed us to obtain both armed and disarmed N-alkylated SBiz donors. These donors showed good reactivity at a variety of activation conditions, and generally provided high yields in glycosylations.

scholarly journals Synthetic avenues towards a tetrasaccharide related toStreptococcus pneumoniaof serotype 6A

2018 ◽  
Vol 14 ◽  
pp. 1095-1102 ◽  
Author(s):  
Aritra Chaudhury ◽  
Mana Mohan Mukherjee ◽  
Rina Ghosh
Keyword(s):  
Building Blocks ◽  
Host Defence ◽  
Oligosaccharide Synthesis ◽  
Positive Bacterium ◽  
Gram Positive ◽  
One Pot ◽  
Streptococcus Pneumonia ◽  
Specific Host ◽  
Life Threatening

Streptococcus pneumonia(SPn) is a Gram-positive bacterium which causes life threatening diseases. The bacteria protect themselves against non-specific host defence by an external polysaccharide (PS) capsule which bears a repeating unit, α-D-Galp(1->3)-α-D-Glcp(1->3)-α-L-Rhap(1->3)-D-Rib (SPn 6A). A closer look at the structure reveals the presence of α-linked galactose and glucose residues. The synthesis of these 1,2-cisglycosidic linkages are considered challenging particularly in the context of a one-pot oligosaccharide synthesis. We have synthesized the aforesaid tetrasaccharide (SPn 6A) based on both stepwise and sequential one-pot glycosylation reactions using easily accessible common building blocks; eventually similar overall yields were obtained in both cases.

Facile preparation of glycosyl donors for oligosaccharide synthesis: 2-azido-2-deoxyhexopyranosyl building blocks

1994 ◽  
Vol 5 (11) ◽  
pp. 2187-2194 ◽  
Author(s):  
Therese Buskas ◽  
Per J. Garegg ◽  
Peter Konradsson ◽  
Jean-Luc Maloisel
Keyword(s):  
Building Blocks ◽  
Oligosaccharide Synthesis ◽  
Facile Preparation ◽  
Glycosyl Donors

Synthesis of Nitrile-Bearing Quaternary Centers via an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy

2019 ◽  
Author(s):  
Sebastien Alazet ◽  
Michael West ◽  
Purvish Patel ◽  
Sophie Rousseaux
Keyword(s):  
Building Blocks ◽  
One Pot ◽  
Quaternary Centers ◽  
Synthetic Intermediates

The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers via a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.<br>

scholarly journals 2-Aryl-6-Polyfluoroalkyl-4-Pyrones as Promising RF-Building-Blocks: Synthesis and Application for Construction of Fluorinated Azaheterocycles

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4415
Author(s):  
Sergey A. Usachev ◽  
Diana I. Nigamatova ◽  
Daria K. Mysik ◽  
Nikita A. Naumov ◽  
Dmitrii L. Obydennov ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Building Blocks ◽  
Oxidative Cyclization ◽  
One Pot ◽  
Synthetic Application ◽  
General Method

A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed on the basis of one-pot oxidative cyclization of (E)-6-aryl-1,1,1-trifluorohex-5-ene-2,4-diones via a bromination/dehydrobromination approach. This strategy was also applied for the preparation of 2-phenyl-6-polyfluoroalkyl-4-pyrones and their 5-bromo derivatives. Conditions of chemoselective enediones bromination were found and the key intermediates of the cyclization of bromo-derivatives to 4-pyrones were characterized. Synthetic application of the prepared 4-pyrones has been demonstrated for the construction of biologically important CF3-bearing azaheterocycles, such as pyrazoles, pyridones, and triazoles.

scholarly journals 1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1214
Author(s):  
Sergey N. Podyachev ◽  
Rustem R. Zairov ◽  
Asiya R. Mustafina
Keyword(s):  
Structural Diversity ◽  
Building Blocks ◽  
Structural Features ◽  
Structure Property ◽  
One Pot ◽  
Arene Ligands ◽  
Structure Property Relationships ◽  
New Type ◽  
Synthetic Routes ◽  
Magnetic Resonance Imaging Mri

The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure–property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.

Access to Unnatural Glycosyl Amino Acid Building Blocks via a One-Pot Ritter Reaction

Synlett ◽  
2005 ◽  
pp. 212-216 ◽  
Author(s):  
Frank Schweizer ◽  
Marlin Penner ◽  
David Taylor ◽  
Danielle Desautels ◽  
Kirk Marat
Keyword(s):  
Amino Acid ◽  
Building Blocks ◽  
Ritter Reaction ◽  
One Pot

Conformationally armed glycosyl donors: reactivity quantification, new donors and one pot reactions

2008 ◽  
pp. 2465 ◽  
Author(s):  
Christian Marcus Pedersen ◽  
Lavinia G. Marinescu ◽  
Mikael Bols
Keyword(s):  
One Pot ◽  
New Donors ◽  
Glycosyl Donors
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