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Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation.
Carbohydr Res. 2016 Jul 22; 430:16-23.CR

Abstract

The O-glycosidation of hydroxysuccinimides and hydroxyphthalimides with a variety of aldose derived propargyl 1,2-orthoesters under the gold(III)-catalyzed glycosidation conditions is reported. A wide range of hydroxysuccinimidyl and hydroxyphthalimidyl glycosides were synthesized from corresponding glycosyl orthoesters including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well.

Authors+Show Affiliations

Department of Chemistry, Indian Institute of Science Education & Research, Pune 411 008, India.Department of Chemistry, Indian Institute of Science Education & Research, Pune 411 008, India.Department of Chemistry, Indian Institute of Science Education & Research, Pune 411 008, India. Electronic address: s.hotha@iiserpune.ac.in.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27162194

Citation

Thadke, Shivaji A., et al. "Facile Synthesis of Aminooxy Glycosides By gold(III)-catalyzed Glycosidation." Carbohydrate Research, vol. 430, 2016, pp. 16-23.
Thadke SA, Neralkar M, Hotha S. Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation. Carbohydr Res. 2016;430:16-23.
Thadke, S. A., Neralkar, M., & Hotha, S. (2016). Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation. Carbohydrate Research, 430, 16-23. https://doi.org/10.1016/j.carres.2016.04.022
Thadke SA, Neralkar M, Hotha S. Facile Synthesis of Aminooxy Glycosides By gold(III)-catalyzed Glycosidation. Carbohydr Res. 2016 Jul 22;430:16-23. PubMed PMID: 27162194.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation. AU - Thadke,Shivaji A, AU - Neralkar,Mahesh, AU - Hotha,Srinivas, Y1 - 2016/04/27/ PY - 2015/12/24/received PY - 2016/04/20/revised PY - 2016/04/22/accepted PY - 2016/5/11/entrez PY - 2016/5/11/pubmed PY - 2017/1/31/medline KW - Chemical synthesis KW - Glycosides KW - Gold catalysis KW - Oligosaccharides SP - 16 EP - 23 JF - Carbohydrate research JO - Carbohydr. Res. VL - 430 N2 - The O-glycosidation of hydroxysuccinimides and hydroxyphthalimides with a variety of aldose derived propargyl 1,2-orthoesters under the gold(III)-catalyzed glycosidation conditions is reported. A wide range of hydroxysuccinimidyl and hydroxyphthalimidyl glycosides were synthesized from corresponding glycosyl orthoesters including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well. SN - 1873-426X UR - https://www.unboundmedicine.com/medline/citation/27162194/Facile_synthesis_of_aminooxy_glycosides_by_gold_III__catalyzed_glycosidation_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(16)30118-5 DB - PRIME DP - Unbound Medicine ER -
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