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Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides.
Carbohydr Res. 2004 Sep 13; 339(13):2197-204.CR

Abstract

Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and alpha-anomeric 2-deoxy glycosides were obtained exclusively.

Authors+Show Affiliations

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.No affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15337447

Citation

Paul, Somak, and Narayanaswamy Jayaraman. "Catalytic Ceric Ammonium Nitrate Mediated Synthesis of 2-deoxy-1-thioglycosides." Carbohydrate Research, vol. 339, no. 13, 2004, pp. 2197-204.
Paul S, Jayaraman N. Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides. Carbohydr Res. 2004;339(13):2197-204.
Paul, S., & Jayaraman, N. (2004). Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides. Carbohydrate Research, 339(13), 2197-204.
Paul S, Jayaraman N. Catalytic Ceric Ammonium Nitrate Mediated Synthesis of 2-deoxy-1-thioglycosides. Carbohydr Res. 2004 Sep 13;339(13):2197-204. PubMed PMID: 15337447.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides. AU - Paul,Somak, AU - Jayaraman,Narayanaswamy, PY - 2004/04/29/received PY - 2004/07/17/revised PY - 2004/07/18/accepted PY - 2004/9/1/pubmed PY - 2005/3/30/medline PY - 2004/9/1/entrez SP - 2197 EP - 204 JF - Carbohydrate research JO - Carbohydr. Res. VL - 339 IS - 13 N2 - Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and alpha-anomeric 2-deoxy glycosides were obtained exclusively. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/15337447/Catalytic_ceric_ammonium_nitrate_mediated_synthesis_of_2_deoxy_1_thioglycosides_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(04)00323-4 DB - PRIME DP - Unbound Medicine ER -