Remote activation concept

Glycoside Synthesis Based on the Remote Activation Concept An Overview... 

The first generation of an O-unprotected glycosyl donor that could be activated based on the remote activation concept was exemplified by 2-pyridylthio p-D-glucopyranoside 1 [10], which could be easily prepared from acetobromoglucose [11]. Treatment of 1 with a variety of alcohols in the presence of mercuric nitrate in acetonitrile solution led, within a few minutes, to the corresponding O-glycosides, with isolated yields and a/p ratios varying from methanol (70 30, 95%), to 2-propanol (62 38 77%), and cyclohexanol (51 49, 75%) Scheme 2. Identical results were obtained when 2-pyrimidinylthio p-D-... 

Scheme 1 The design of glycosyl 2-pyridylcarbonate or glycosyl 2-thiopyridylcarbonate (TOP-CAT) donors based on the remote activation concept.

K. Koidc, M. Ohno, and S. Kobayashi, A new glycosylation reaction based on a remote activation concept Glycosyl 2-pyridinecarboxylate as a novel glycosyl donor. Tetrahedron Lett. 32 7065 (1991). 

Peterson olefination, 23 i, 232, 249, 250 Phyllanthocin, 570 Protein folding, 486 Pseudomonic acid, 226 Remote activation concept, 381, 383, 389,413... 

B. Lou, G. V. Reddy, H. Wang, and S. Hanessian, Glycoside and oligosaccharide synthesis with unprotected glycosyl donors based on the remote activation concept, in S. Hanessian, (Ed.), Preparative Carbohydrate Chemistry, Marcel Dekker, Inc., New York, 1997, p. 389. 

Hanessian, S. Glycoside synthesis based on the remote activation concept an overview. In Preparative Carbohydrate Chemistry. Hanessian, S. (ed.) Marcel Dekker New York, 1997, pp. 381-388. 

---