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Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides.
Carbohydr Res. 2007 Jul 23; 342(10):1305-14.CR

Abstract

The synthesis of either anomers of aryl 2-deoxy-D-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The alpha-anomers form as the major product when thioglycosides react with differently substituted phenols and naphthols, in the presence of N-iodosuccinimide/triflic acid. On the other hand, reaction of the thioglycosides with bromine initially, followed by reaction with aryloxy anions lead to aryl 2-deoxy-beta-D-glycosides with high specificities.

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

17477910

Citation

Paul, Somak, and Narayanaswamy Jayaraman. "Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides From 2-deoxy-1-thioglycosides." Carbohydrate Research, vol. 342, no. 10, 2007, pp. 1305-14.
Paul S, Jayaraman N. Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides. Carbohydr Res. 2007;342(10):1305-14.
Paul, S., & Jayaraman, N. (2007). Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides. Carbohydrate Research, 342(10), 1305-14.
Paul S, Jayaraman N. Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides From 2-deoxy-1-thioglycosides. Carbohydr Res. 2007 Jul 23;342(10):1305-14. PubMed PMID: 17477910.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides. AU - Paul,Somak, AU - Jayaraman,Narayanaswamy, Y1 - 2007/03/01/ PY - 2006/12/16/received PY - 2007/02/21/revised PY - 2007/02/25/accepted PY - 2007/5/5/pubmed PY - 2007/7/26/medline PY - 2007/5/5/entrez SP - 1305 EP - 14 JF - Carbohydrate research JO - Carbohydr. Res. VL - 342 IS - 10 N2 - The synthesis of either anomers of aryl 2-deoxy-D-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The alpha-anomers form as the major product when thioglycosides react with differently substituted phenols and naphthols, in the presence of N-iodosuccinimide/triflic acid. On the other hand, reaction of the thioglycosides with bromine initially, followed by reaction with aryloxy anions lead to aryl 2-deoxy-beta-D-glycosides with high specificities. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/17477910/Synthesis_of_aryl_2_deoxy_D_lyxo/arabino_hexopyranosides_from_2_deoxy_1_thioglycosides_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(07)00121-8 DB - PRIME DP - Unbound Medicine ER -