Action of Base on Methyl 6-Thio- (and 6-Deoxy-) 2- O -Methanesulfonyl-α- d -Glucopyranoside Derivatives 1
✍ Scribed by Izquierdo, Isidoro; Rodríguez, Miguel; Plaza, María T.; Pleguezuelos, Julia
- Book ID
- 121414858
- Publisher
- Taylor and Francis Group
- Year
- 1998
- Tongue
- English
- Weight
- 751 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0732-8303
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In previous papers, we have reported on the synthesis of 2,6-[1], 3,6-[2], and 4,6-thioanhydro sugars [3] that were shown to be important intermediates for the enantiospecific preparation of polyhydroxythianes and thiolanes, structurally related to the potent glycosidase inhibitors polyhydroxypiperi
ions of some methyl-6-deoxy-6-bromo-a-D-glucopyranoside derivatives are discussed. Elimination of MeOH resulting in the glycosidyl cation is the predominant reaction of the [ M + HI+ ion. This process is completely suppressed during CID of the metal-cationized species, which, surprisingly, show elim