Use of the [.beta.-(trimethylsilyl)ethoxy]methyl (SEM) protecting group in carbohydrate chemistry. Fully functionalized rhamnose acceptors and donors for use in oligosaccharide synthesis [Erratum to document cited in CA112(17):158770s]

1990 ◽  
Vol 55 (17) ◽  
pp. 5180-5180
Author(s):  
B. Mario Pinto ◽  
Michiel M. W. Buiting ◽  
Kerry B. Reimer
Keyword(s):  
Oligosaccharide Synthesis ◽  
Protecting Group ◽  
Carbohydrate Chemistry

A New Oligosaccharide Synthesis Using Special Hydroxy Protecting Group.

ChemInform ◽  
2004 ◽  
Vol 35 (24) ◽  
Author(s):  
Shiro Komba ◽  
Motomitsu Kitaoka ◽  
Takafumi Kasumi
Keyword(s):  
Oligosaccharide Synthesis ◽  
Protecting Group

Picoloyl-Protecting Group in Oligosaccharide Synthesis

2017 ◽  
pp. 3-10 ◽  
Author(s):  
Michael P. Mannino ◽  
Jagodige P. Yasomanee ◽  
Alexei V. Demchenko ◽  
Venukumar Patteti
Keyword(s):  
Oligosaccharide Synthesis ◽  
Protecting Group

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.

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