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

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

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

One-Pot Oligosaccharide Synthesis: Reactivity Tuning by Post-Synthetic Modification of Aglycon.

ChemInform ◽  
2004 ◽  
Vol 35 (51) ◽  
Author(s):  
Lijun Huang ◽  
Zhen Wang ◽  
Xuefei Huang
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

2003 ◽  
Vol 42 (38) ◽  
pp. 4657-4660 ◽  
Author(s):  
Thomas K. Ritter ◽  
Kwok-Kong T. Mong ◽  
Haitian Liu ◽  
Takuji Nakatani ◽  
Chi-Huey Wong
Keyword(s):  
Natural Products ◽  
Oligosaccharide Synthesis ◽  
One Pot
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