One-Pot Azidochlorination of Glycals

Plattner C, Höfener M, Sewald N (2011)
Organic Letters 13(4): 545-547.

Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
; ;
Abstract / Bemerkung
A simple one-pot azidochlorination for the preparation of nitrogen-containing Kwoenigs-Knorr glycosyl donors proceeds upon reaction of protected glycals with sodium azide, ferric chloride, and hydrogen peroxide. Different mono- and disaccharide galactals and glucals are converted in a highly alpha-selective manner to the 2-azido glycosyl chlorides. Starting from disaccharide galactals, building blocks for the synthesis of the T-antigen are obtained in a straightforward manner. The simplicity of the reaction conditions allows for an efficient and scalable alpha-selective synthesis of 2-azido substituted glycosyl chlorides.
Organic Letters


Plattner C, Höfener M, Sewald N. One-Pot Azidochlorination of Glycals. Organic Letters. 2011;13(4):545-547.
Plattner, C., Höfener, M., & Sewald, N. (2011). One-Pot Azidochlorination of Glycals. Organic Letters, 13(4), 545-547. doi:10.1021/ol102750h
Plattner, C., Höfener, M., and Sewald, N. (2011). One-Pot Azidochlorination of Glycals. Organic Letters 13, 545-547.
Plattner, C., Höfener, M., & Sewald, N., 2011. One-Pot Azidochlorination of Glycals. Organic Letters, 13(4), p 545-547.
C. Plattner, M. Höfener, and N. Sewald, “One-Pot Azidochlorination of Glycals”, Organic Letters, vol. 13, 2011, pp. 545-547.
Plattner, C., Höfener, M., Sewald, N.: One-Pot Azidochlorination of Glycals. Organic Letters. 13, 545-547 (2011).
Plattner, Carolin, Höfener, Michael, and Sewald, Norbert. “One-Pot Azidochlorination of Glycals”. Organic Letters 13.4 (2011): 545-547.

14 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.
Park Y, Harper KC, Kuhl N, Kwan EE, Liu RY, Jacobsen EN., Science 355(6321), 2017
PMID: 28082586
The interdomain flexible linker of the polypeptide GalNAc transferases dictates their long-range glycosylation preferences.
de Las Rivas M, Lira-Navarrete E, Daniel EJP, Compañón I, Coelho H, Diniz A, Jiménez-Barbero J, Peregrina JM, Clausen H, Corzana F, Marcelo F, Jiménez-Osés G, Gerken TA, Hurtado-Guerrero R., Nat Commun 8(1), 2017
PMID: 29208955
Biosynthetic and synthetic access to amino sugars.
Skarbek K, Milewska MJ., Carbohydr Res 434(), 2016
PMID: 27592039
Synthesis of the tetrasaccharide outer core fragment of Burkholderia multivorans lipooligosaccharide.
Ziaco M, De Castro C, Silipo A, Corsaro MM, Molinaro A, Iadonisi A, Lanzetta R, Parrilli M, Bedini E., Carbohydr Res 403(), 2015
PMID: 24933233
Glycopeptide analogues of PSGL-1 inhibit P-selectin in vitro and in vivo.
Krishnamurthy VR, Sardar MY, Ying Y, Song X, Haller C, Dai E, Wang X, Hanjaya-Putra D, Sun L, Morikis V, Simon SI, Woods RJ, Cummings RD, Chaikof EL., Nat Commun 6(), 2015
PMID: 25824568
Dynamic interplay between catalytic and lectin domains of GalNAc-transferases modulates protein O-glycosylation.
Lira-Navarrete E, de Las Rivas M, Compañón I, Pallarés MC, Kong Y, Iglesias-Fernández J, Bernardes GJ, Peregrina JM, Rovira C, Bernadó P, Bruscolini P, Clausen H, Lostao A, Corzana F, Hurtado-Guerrero R., Nat Commun 6(), 2015
PMID: 25939779
Thermodynamic Switch in Binding of Adhesion/Growth Regulatory Human Galectin-3 to Tumor-Associated TF Antigen (CD176) and MUC1 Glycopeptides.
Rodriguez MC, Yegorova S, Pitteloud JP, Chavaroche AE, André S, Ardá A, Minond D, Jiménez-Barbero J, Gabius HJ, Cudic M., Biochemistry 54(29), 2015
PMID: 26129647
Serine versus threonine glycosylation with α-O-GalNAc: unexpected selectivity in their molecular recognition with lectins.
Madariaga D, Martínez-Sáez N, Somovilla VJ, García-García L, Berbis MÁ, Valero-Gónzalez J, Martín-Santamaría S, Hurtado-Guerrero R, Asensio JL, Jiménez-Barbero J, Avenoza A, Busto JH, Corzana F, Peregrina JM., Chemistry 20(39), 2014
PMID: 25111627
Influence of sequential modifications and carbohydrate variations in synthetic AFGP analogues on conformation and antifreeze activity.
Nagel L, Budke C, Erdmann RS, Dreyer A, Wennemers H, Koop T, Sewald N., Chemistry 18(40), 2012
PMID: 22930587
Antifreeze glycopeptide diastereomers.
Nagel L, Budke C, Dreyer A, Koop T, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209499
Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers.
Nagel L, Plattner C, Budke C, Majer Z, DeVries AL, Berkemeier T, Koop T, Sewald N., Amino Acids 41(3), 2011
PMID: 21603949


Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®


PMID: 21244046
PubMed | Europe PMC

Suchen in

Google Scholar