Strategies for One‐pot Synthesis of Oligosaccharides

Yang, Bo; Yoshida, Keisuke; Huang, Xuefei

doi:10.1002/9781119006435.ch6

Cited by 2 publications

(1 citation statement)

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“…For the success of any one-pot glycosylation, it is necessary that every reaction goes to completion, giving mainly one product in excellent yield and stereoselectivity, and that the protecting groups as well as generated side products are compatible with all the reagents that are added in the same pot. Over the past 20 years, a variety of novel one-pot glycosylation protocols have been established. ,,,,− The one-pot glycosylation approach exploits subtle reactivity differences of glycosyl donors or acceptors, and it is most often performed from the nonreducing end to the reducing end. However, it can also be carried out from the reducing end to the nonreducing end or through a combination of strategies.…”

Section: Glycosylationmentioning

confidence: 99%

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

et al. 2018

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Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play significant roles in a variety of vital biological processes. Access to unique and homogeneous carbohydrate materials is important to understand their physical properties, biological functions, and disease-related features. It is difficult to isolate carbohydrates in acceptable purity and amounts from natural sources. Therefore, complex saccharides with well-defined structures are often most conviently accessed through chemical syntheses. Two major hurdles, regioselective protection and stereoselective glycosylation, are faced by carbohydrate chemists in synthesizing these highly complicated molecules. Over the past few years, there has been a radical change in tackling these problems and speeding up the synthesis of oligosaccharides. This is largely due to the development of one-pot protection, one-pot glycosylation, and one-pot protection-glycosylation protocols and streamlined approaches to orthogonally protected building blocks, including those from rare sugars, that can be used in glycan coupling. In addition, new automated strategies for oligosaccharide syntheses have been reported not only for program-controlled assembly on solid support but also by the stepwise glycosylation in solution phase. As a result, various sugar molecules with highly complex, large structures could be successfully synthesized. To summarize these recent advances, this review describes the methodologies for one-pot protection and their one-pot glycosylation into the complex glycans and the chronological developments associated with automated syntheses of oligosaccharides.

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