Patent ID: 6555677
Filing Date: 2003-04-29
Classification: A61P,C07H

Abstract:
A process for the preparation of a compound of Formula I, whereinQ is O, Nâ€”R, S, or CH2; X1 and X2 are independently selected from: 1) H, 2) halogen, 3) OH, 4) CN, 5) NC, 6) CF3, 7) (C&boxH;O)NO2, 8) (C&boxH;O)C1-C6 alkyl, 9) (C&boxH;O)OC1-C6 alkyl, 10) OCH2OCH2CH2Si(CH3)3, 11) NO2, 12) 9-fluorenylmethylcarbonyl, 13) NR5R6, 14) OC1-C6 alkyl, 15) C1-C6 alkyl, 16) C1-C6 alkylenearyl, and 17) OC1-C6 alkylenearyl; R and R1 are independently: 1) H, 2) (C&boxH;O)C1-C6 alkyl, 3) (C&boxH;O)CF3, 4) (C&boxH;O)OC1-C6 alkyl, 5) 9-fluorenylmethylcarbonyl, 6) a furanose group, or 7) a pyranose group, so long as one of R and R1 is a furanose group or a pyranose group; R2 and R3 are independently OH or H, or R2 and R3 are taken together to form an oxo group; R4 is: 1) H, 2) C1-C10 alkyl, 3) CHO, 4) (C&boxH;O)C1-C10 alkyl, 5) (C&boxH;O)OC1-C10 alkyl, 6) C0-C10 alkylenearyl, or 7) C0-C10 alkylene-NR5R6; R5 and R6 are independently: 1) H, 2) (C1-C8 alkyl)â€”(R7)2, 3) (C&boxH;O)O(C1-C8 alkyl), 4) 9-fluorenylmethylcarbonyl, 5) OCH2OCH2CH2Si(CH3)3, 6) (C&boxH;O)(C1-C8 alkyl), 7) (C&boxH;O)CF3, or 8) (C2-C8 alkenyl)â€”(R7)2, or R5 and R6 are taken together with the nitrogen to which they are attached to form N-phthalimido; R7 is: 1) H, 2) OH, 3) OC1-C6 alkyl, or 4) aryl, said aryl optionally substituted with up to two groups selected from OH, O(C1-C6 alkyl), and (C1-C3 alkylene)â€”OH; â€ƒwhich comprises the steps of: (a) reacting a furanose or a pyranose with an activating reagent to produce an activated sugar; and (b) coupling the activated sugar with a compound of Formula IV â€ƒwherein R1a is H if Q is O, S, CH2, or Nâ€”R and R is not H, otherwise R1a is selected from R1; â€ƒin the presence of an aqueous solution of alkali hydroxide and a phase transfer catalyst in a biphasic system to produce the compound of Formula I.