Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/indium-iii-triflate-catalyzed-glycosylation-through-an-ambient-ncVROoMjA0
References (46)
-
P. Hultin (2005)
Bioactive C-glycosides from bacterial secondary metabolism.Current topics in medicinal chemistry, 5 14
-
E. Juaristi, G. Cuevas (1992)
Recent studies of the anomeric effectTetrahedron, 48
-
P. Tiseni, R. Peters (2008)
Lewis acid-Lewis base catalyzed enantioselective hetero-Diels-Alder reaction for direct access to delta-lactones.Organic letters, 10 10
-
Philip Adero, H. Amarasekara, Peng Wen, L. Bohé, D. Crich (2018)
The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.Chemical reviews, 118 17
-
A. Orita, Chiaki Tanahashi, A. Kakuda, J. Otera* (2000)
Highly Efficient and Versatile Acylation of Alcohols with Bi(OTf)(3) as Catalyst.Angewandte Chemie, 39 16
-
D. Crich (2010)
Mechanism of a chemical glycosylation reaction.Accounts of chemical research, 43 8
-
R. Freitas (2014)
New Uses for Indium(III) ChlorideSynlett, 25
-
Xiao-ping Chen, Qiaoling Wang, Biao Yu (2016)
Gold(i)-catalyzed C-glycosylation of glycosyl ortho-alkynylbenzoates: the role of the moisture sequestered by molecular sieves.Chemical communications, 52 82
-
M. McKay, Benjamin Naab, G. Mercer, Hien Nguyen (2009)
Selective formation of beta-O-aryl glycosides in the absence of the C(2)-ester neighboring group.The Journal of organic chemistry, 74 13
-
P. Crocker, T. Feizi (1996)
Carbohydrate recognition systems: functional triads in cell-cell interactions.Current opinion in structural biology, 6 5
-
J. Paradies (2010)
Synthesis of DivinylsulfidesSynthesis, 2010
-
Hong-Bo Qin, Noriyuki Yamagiwa, S. Matsunaga, M. Shibasaki (2007)
Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides.Angewandte Chemie, 46 3
-
K. Toshima (2000)
Glycosyl fluorides in glycosidations.Carbohydrate research, 327 1-2
-
P. Champagne, Julien Pomarole, M. Thérien, Yasmine Benhassine, S. Beaulieu, Claude Legault, J. Paquin (2013)
Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding.Organic letters, 15 9
-
F. Avci, Xiangming Li, M. Tsuji, Dennis Kasper (2011)
A novel mechanism for glycoconjugate vaccine activation of the adaptive immune systemNature medicine, 17
-
Danica Galonić, D. Gin (2007)
Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccinesNature, 446
-
C. Bertozzi, and Kiessling (2001)
Chemical GlycobiologyScience, 291
-
P. Rudd, T. Elliott, P. Cresswell, I. Wilson, R. Dwek (2001)
Glycosylation and the immune system.Science, 291 5512
-
N. Taniguchi, T. Endo, G. Hart, P. Seeberger, P. Seeberger, Chi‐Huey Wong, Chi‐Huey Wong (2015)
Glycoscience: Biology and Medicine -
Tobias Frihed, M. Bols, C. Pedersen (2015)
Mechanisms of glycosylation reactions studied by low-temperature nuclear magnetic resonance.Chemical reviews, 115 11
-
S. Yajima, Tsuyoshi Saitoh, Kohei Kawa, Kensuke Nakamura, H. Nagase, Y. Einaga, S. Nishiyama (2016)
Asymmetric induction in cyclohexadienones carrying α-d-glucopyranosyl moietyTetrahedron, 72
-
Fulong Li, C. Ding, Meining Wang, Qizheng Yao, A. Zhang (2011)
InBr3-catalyzed glycosidation of glycals with arylamines: an alternative approach to access 4-aminocyclopent-2-enones.The Journal of organic chemistry, 76 8
-
Alessandro and, A. Marra (2000)
Methods for anomeric carbon-linked and fused sugar amino Acid synthesis: the gateway to artificial glycopeptides.Chemical reviews, 100 12
-
Zhan‐Hui Zhang (2005)
Indium Tribromide: A Water-Tolerant Green Lewis AcidSynlett, 2005
-
S. Manabe, Yukishige Ito (2013)
Hafnium(IV) tetratriflate as a glycosyl fluoride activation reagent.The Journal of organic chemistry, 78 9
-
(2007)
Acetal glucose 13 was stirred for 24 h with a catalytic amount of BiCl 3 , InBr 3 , In ( OTf ) 3 . [ 14 ] -
M. Nardi, N. Cano, A. Nino, M. Gioia, L. Maiuolo, M. Oliverio, A. Santiago, D. Sorrentino, A. Procopio (2017)
An eco-friendly tandem tosylation/Ferrier N-glycosylation of amines catalyzed by Er(OTf)3 in 2-MeTHFTetrahedron Letters, 58
-
T. Ma, Chang-Wu Li, Zhan‐Xin Zhang, Zhao-yan Wang, Lan Yu, Weihua Xue (2017)
Indium(III) Iodide-Catalyzed Stereoselective Synthesis of β-Glucopyranosides by Using a Glucosyl Fluoride Donor with 2-O-Benzoyl-3,4,6-Tri-O-Benzyl ProtectionSynlett, 28
-
S. Kobayashi, T. Busujima, S. Nagayama (2000)
A Novel Classification of Lewis Acids on the Basis of Activity and SelectivityChemistry: A European Journal, 6
-
A. Mattson, Anna Michel, M. Cloninger (2012)
Using In(III) as a promoter for glycosylation.Carbohydrate research, 347 1
-
Jose Fernández, Cristina, Martínez, Wifredo Ricart (2018)
The version of record : -
(2008)
Carbohydrates in Chemistry and Biology, Chapter 17 (Eds -
N. Poomathi, P. Perumal, S. Ramakrishna (2017)
An efficient and eco-friendly synthesis of 2-pyridones and functionalized azaxanthone frameworks via indium triflate catalyzed domino reactionGreen Chemistry, 19
-
B. Gregg, K. Golden, J. Quinn (2007)
Indium(III) trifluoromethanesulfonate as an efficient catalyst for the deprotection of acetals and ketals.The Journal of organic chemistry, 72 15
-
A. Varki (1993)
Biological roles of oligosaccharides: all of the theories are correctGlycobiology, 3
-
Thierry Ollevier (2013)
New trends in bismuth-catalyzed synthetic transformations.Organic & biomolecular chemistry, 11 17
-
J. Štambaský, Michal Hocek, P. Kočovský (2009)
C-nucleosides: synthetic strategies and biological applications.Chemical reviews, 109 12
-
E. Palmacci, P. Seeberger (2001)
Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates.Organic letters, 3 10
-
Amol Vibhute, Arun Dhaka, Vignesh Athiyarath, K. Sureshan (2016)
A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors† †Electronic supplementary information (ESI) available: Synthetic procedures, characterization and spectral data for all new compounds. See DOI: 10.1039/c6sc00633gChemical Science, 7
-
S. Gruner, E. Locardi, E. Lohof, H. Kessler (2002)
Carbohydrate-based mimetics in drug design: sugar amino acids and carbohydrate scaffolds.Chemical reviews, 102 2
-
S. Blanksby, G. Ellison (2003)
Bond dissociation energies of organic molecules.Accounts of chemical research, 36 4
-
Yuwen Li, G. Wei, Biao Yu (2006)
Aryl C-glycosylation of phenols with glycosyl trifluoroacetimidates.Carbohydrate research, 341 16
-
S. Kobayashi, C. Ogawa (2006)
New entries to water-compatible Lewis acids.Chemistry, 12 23
-
T. Mukaiyama, Y. Hashimoto, S. Shoda (1983)
STEREOSELECTIVE SYNTHESIS OF 1,2-CIS-GLYCOFURANOSIDES USING GLYCOFURANOSYL FLUORIDESChemistry Letters, 12
-
C. Roux, J. Dubac (2002)
Bismuth(III) Chloride and Triflate: Novel Catalysts for Acylation and Sulfonylation Reactions. Survey and Mechanistic AspectsChemInform, 33
-
Thierry Ollevier, Guillaume Lavie-Compin (2002)
An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichlorideTetrahedron Letters, 43
- Publisher
- Wiley
- Copyright
- © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201800582
- Publisher site
- See Article on Publisher Site
Abstract
A highly efficient catalytic glycosylation using glycosyl fluoride in the presence of a mild and non‐toxic Lewis acid, indium(III) triflate, was achieved. The facile and convenient glycosylation procedure does not require pre‐activation steps, pre‐distillation, or cumbersome work‐up process, and it was compatible with a broad range of alcohol acceptors under ambient conditions. Furthermore, the stereoselective C‐glycosylation smoothly proceeded under the same conditions.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Jan 1, 2019
Keywords: ; ; ; ;