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Gold Catalyzed Glycosylation for Glycoconjugates (3G) |
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Research Interests Gold-catalyzed Glycosidation Laboratory (G2L)
s.hotha@iiserpune.ac.in +91 20 2590 8015, +91 20 2589 9790 (fax), +91 9823677254
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Gold carbohydrates are intricately connected with the development of civilization and humans. However, the amalgamation of the chemistries of gold and carbohydrates was not explored until the discovery of the transglycosylation protocol using alkynalated glycosides as glycosyl donors by our group. Propargyl glycosides can be activated at 70 oC with 5mol% of AuX3 (X=Cl or Br) whereas the Ethynylcyclohexyl glycosides can be activated at room temperature with 5mol% each of AuX3 (X=Cl or Br) and AgSbF6 in acetonitrile. Both of these protocols give a,b-mixture of pyranosides except in case of mannose where only a-mannopyranosides are observed. Propargyl 1,2-O-orthoesters can be utilized for the synthesis of 1,2-trans pyranosides at room temperature using catalytic amount of gold(III) salts. |
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Quite recent work on furanosyl donors showed that the propargyl orthoesters can be utilized for the synthesis of 1,2-trans furanosides and 1,2-cis furanosides can be easily synthesized by oxidoreduction strategy in a bioinspired fashion. Application of these methods for the synthesis of carbohydrate epitopes of infectious bacteria is currently investigated in the group. |
