Concepedia

Intermolecular Hydrogen‐Bonding Pattern of a Glycosyl Donor: The Key to Understanding the Outcome of Sialylation

L. O. Kononov, N. N. Malysheva, Elena G. Kononova, A. V. Orlova

European Journal of Organic Chemistry · 2008 · 53 citations · 16 references

DOI

Concepts

Abstract

Abstract Changes in the hydrogen‐bonding pattern in solutions of glycosyl donor induced by the addition of external amides/imides or by concentration changes influence the yield and stereoselectivity of sialylation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

References

16

Why Are the Hydroxy Groups of Partially Protected <i>N</i>-Acetylglucosamine Derivatives Such Poor Glycosyl Acceptors, and What Can Be Done about It? A Comparative Study of the Reactivity of <i>N</i>-Acetyl-, <i>N</i>-Phthalimido-, and 2-Azido-2-deoxy-glucosamine Derivatives in Glycosylation. 2-Picolinyl Ethers as Reactivity-Enhancing Replacements for Benzyl Ethers

David Crich, Vadim Dudkin · Journal of the American Chemical Society · 2001 · 215 citations

, , +16

Stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid

Alberto Marra, Pierre Sînaÿ · Carbohydrate Research · 1989 · 195 citations

, , +6

Glycosylation Using Methylthioglycosides of<i>N</i>-Acetylneuraminic Acid and Dimethyl(Methylthio)Sulfonium Triflate

Osamu Kanie, Makoto Kiso, Akira Hasegawa · Journal of Carbohydrate Chemistry · 1988 · 175 citations

, , +14

<i>O</i>-Sialylation with<i>N</i>-Acetyl-5-<i>N</i>,4-<i>O</i>-Carbonyl-Protected Thiosialoside Donors in Dichloromethane:  Facile and Selective Cleavage of the Oxazolidinone Ring

David Crich, Wenju Li · The Journal of Organic Chemistry · 2007 · 170 citations · Full text

, , +13

Communication: Synthetic Studies on Sialoglycoconjugates 25: Reactivity of Glycosyl Promoters in α-Glycosylation of N-Acetyl-Neuraminic Acid with the Primary and Secondary Hydroxyl Groups in the Suitably Protected Galactose and Lactose Derivatives

Akira Hasegawa, Takao Nagahama, Hitoshi Ohki et al. · Journal of Carbohydrate Chemistry · 1991 · 161 citations

, , +16