N-Benzyl-2,3-oxazolidinone as a Glycosyl Donor for Selective α-Glycosylation and One-Pot Oligosaccharide Synthesis Involving 1,2-cis-Glycosylation

2006 ◽  
Vol 128 (33) ◽  
pp. 10666-10667 ◽  
Author(s):  
Shino Manabe ◽  
Kazuyuki Ishii ◽  
Yukishige Ito
Keyword(s):  
Oligosaccharide Synthesis ◽  
One Pot ◽  
Glycosyl Donor

scholarly journals A One-Pot Approach to Novel Pyridazine C-Nucleosides

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2341
Author(s):  
Flavio Cermola ◽  
Serena Vella ◽  
Marina DellaGreca ◽  
Angela Tuzi ◽  
Maria Rosaria Iesce
Keyword(s):  
Organic Chemistry ◽  
Research Field ◽  
Modified Nucleosides ◽  
Protecting Groups ◽  
Coupling Reactions ◽  
One Pot ◽  
Pharmacological Interest ◽  
Classical Methodology ◽  
Glycosyl Donor ◽  
Neutral Conditions

The synthesis of glycosides and modified nucleosides represents a wide research field in organic chemistry. The classical methodology is based on coupling reactions between a glycosyl donor and an acceptor. An alternative strategy for new C-nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone. This approach is applied to obtain novel pyridazine C-nucleosides starting with 2- and 3-(ribofuranosyl)furans. It is based on singlet oxygen [4+2] cycloaddition followed by reduction and hydrazine cyclization under neutral conditions. The mild three-step one-pot procedure leads stereoselectively to novel pyridazine C-nucleosides of pharmacological interest. The use of acetyls as protecting groups provides an elegant direct route to a deprotected new pyridazine C-nucleoside.

scholarly journals One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides

2019 ◽  
Vol 91 (9) ◽  
pp. 1451-1470 ◽  
Author(s):  
Rita Pal ◽  
Anupama Das ◽  
Narayanaswamy Jayaraman
Keyword(s):  
Acid Catalysis ◽  
Oligosaccharide Synthesis ◽  
Protecting Group ◽  
Functional Importance ◽  
Central Importance ◽  
One Pot ◽  
Active Method ◽  
Powerful Approach ◽  
Oxocarbenium Ion ◽  
Allyl Glycoside

Abstract Chemical glycosylations occupy a central importance to synthesize tailor-made oligo- and polysaccharides of functional importance. Generation of the oxocarbenium ion or the glycosyl cation is the method of choice in order to form the glycosidic bond interconnecting a glycosyl moiety with a glycosyl/aglycosyl moiety. A number of elegant methods have been devised that allow the glycosyl cation formation in a fairly stream-lined manner to a large extent. The latent-active method provides a powerful approach in the protecting group controlled glycosylations. In this context, allyl glycosides have been developed to meet the requirement of latent-active reactivities under appropriate glycosylation conditions. Radical halogenation provides a newer route of activation of allyl glycosides to an activated allylic glycoside. Such an allylic halide activation subjects the glycoside reactive under acid catalysis, leading to the conversion to a glycosyl cation and subsequent glycosylation with a number of acceptors. The complete anomeric selectivity favoring the 1,2-trans-anomeric glycosides points to the possibility of a preferred conformation of the glycosyl cation. This article discusses about advancements in the selectivity of glycosylations, followed by delineating the allylic halogenation of allyl glycoside as a glycosylation method and demonstrates synthesis of a repertoire of di- and trisaccharides, including xylosides, with varied protecting groups.

One-Pot Oligosaccharide Synthesis Exploiting Solvent Reactivity Effects

2000 ◽  
Vol 2 (24) ◽  
pp. 3881-3882 ◽  
Author(s):  
Martina Lahmann ◽  
Stefan Oscarson
Keyword(s):  
Oligosaccharide Synthesis ◽  
One Pot

scholarly journals Application of the Superarmed Glycosyl Donor to Chemoselective Oligosaccharide Synthesis

2008 ◽  
Vol 10 (11) ◽  
pp. 2107-2110 ◽  
Author(s):  
Laurel K. Mydock ◽  
Alexei V. Demchenko
Keyword(s):  
Oligosaccharide Synthesis ◽  
Glycosyl Donor

Programmable One-Pot Oligosaccharide Synthesis

1999 ◽  
Vol 121 (4) ◽  
pp. 734-753 ◽  
Author(s):  
Zhiyuan Zhang ◽  
Ian R. Ollmann ◽  
Xin-Shan Ye ◽  
Ralf Wischnat ◽  
Timor Baasov ◽  
...  
Keyword(s):  
Oligosaccharide Synthesis ◽  
One Pot

A Programmable One-Pot Oligosaccharide Synthesis for Diversifying the Sugar Domains of Natural Products: A Case Study of Vancomycin.

ChemInform ◽  
2003 ◽  
Vol 34 (49) ◽  
Author(s):  
Thomas K. Ritter ◽  
Kwok-Kong T. Mong ◽  
Haitian Liu ◽  
Takuji Nakatani ◽  
Chi-Huey Wong
Keyword(s):  
Natural Products ◽  
Oligosaccharide Synthesis ◽  
One Pot

scholarly journals Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

10.3791/59987 ◽  
2019 ◽  
Author(s):  
Cheng-Wei Cheng ◽  
Yixuan Zhou ◽  
Wen-Harn Pan ◽  
Supriya Dey ◽  
Chung-Yi Wu ◽  
...  
Keyword(s):  
Oligosaccharide Synthesis ◽  
One Pot
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