主权项 |
1. A method of forming C-aryl glucoside compounds comprising reacting a compound of Formula (IV) wherein ALG is an acid labile protecting group, with a glycosidation reagent to form the compound of Formula (V) reacting the compound of Formula (V) with an acylating reagent to form a compound of Formula (VI)and
reacting the compound of Formula (VI) with a reducing reagent to form a compound of Formula (VII) wherein
R1 is selected from the group consisting of hydrogen, hydroxy, bromine, chlorine, fluorine, alkyl, alkoxy, alkylthio, and arylthio, where p is an integer from 1 to 4, and with the proviso that bromine, chlorine and fluorine, when present, are only present in at least one of the 3-, 4- and 5-positions;R2 is selected from the group consisting of hydrogen, hydroxy, chlorine, fluorine, alkyl, alkoxy, and alkylthio, where q is an integer from 1 to 5; andA is selected from the group consisting of a covalent bond, O, S, NH, and (CH2)n where n is an integer from 1 to 3,with the proviso that when A is in the 4-position, R1 is not bromine;with the proviso that when one of R1 is bromine; and
if A is in the 3- or 6-position, then bromine is in the 5-position,if A is in the 2- or 5-position, then bromine is in the 3-position, andwhen bromine is in the 3-position, and A is in the 2- or 5-position, then R1 groups in the 4- and 6-positions are the same and are not bromine, chlorine or fluorine, andwhen bromine is in the 5-position, and A is in the 3- or 6-position, then R1 groups in the 2- and 4-positions are the same and are not bromine, chlorine or fluorine;R3 is selected from the group consisting of alkoxy, alkenyloxy, alkylthio and alkenylthio; andAC is an acyl protecting group. |