69534-71-0Relevant articles and documents
Syntheses and NMR characterizations of epimeric 4-deoxy-4-fluoro carbohydrates
Subotkowski, Witold,Friedrich, Dirk,Weiberth, Franz J.
, p. 2323 - 2326 (2011/12/04)
The synthesis and NMR characterizations of 1,2,3,6-tetra-O-benzoyl-4-deoxy- 4-fluoro-β-D-galactopyranoside, the 4-deoxy-4-fluoro epimer of an intermediate in the synthesis of a drug substance, needed for use as a potential impurity standard and to confirm the stereoselectivity of a key fluorination step, are described.
Process development of selectively benzoylated and fluorinated glycosyl donors
Weiberth, Franz J.,Gill, Harpal S.,Jiang, Ying,Lee, George E.,Lienard, Philippe,Pemberton, Clive,Powers, Matthew R.,Subotkowski, Witold,Tomasik, Witold,Vanasse, Benoit J.,Yu, Yong
, p. 623 - 631 (2011/07/30)
Route selection, process development and large-scale preparation of selectively benzoylated and fluorinated d-glucopyranoses, required as glycosyl donors for the synthesis of the SGLT inhibitor SAR7226, are discussed.
Unsaturated Carbohydrates. Part 22. Alkenes from 5-Bromohexopyranose Derivatives
Blattner, Regine,Ferrier, Robert J.,Tyler, Peter C.
, p. 1535 - 1539 (2007/10/02)
Base-catalysed elimination of hydrogen bromide from 5-bromo-β-D-glucopyranose penta-acetate and penta-benzoate gives predominantly the endocyclic products, whereas treatment with zinc-acetic acid affords a means of obtaining the exocyclic 6-deoxy-5-enose esters.All eight alkenes obtainable from these two bromo-compounds are reported together with their 1H and 13C n.m.r. spectra.Unsaturated compounds derived from penta-O-benzoyl-5-bromo-α-D-glucopyranose and acetylated 5-bromouronates are also reported.The conformations of all the alkenes are discussed and, in one case, the influences of the anomeric and allylic effects can be compared.
