公开(公告)号：EP0647235A1

公开(公告)日：1995-04-12

申请号：EP93911560.0

申请日：1993-04-02

申请人： PFIZER INC.

发明人： BUSCH, Frank, R. ,  GOGGIN, Kathleen, D. ,  LAMBERT, John, F. ,  SHINE, Russell, J. ,  WALINSKY, Stanley, W.

IPC分类号： A61K31 ,  C07J17 ,  C07J71

CPC分类号： C07J71/0005 ,  C07J17/005

摘要： A process for the synthesis of 1-O-steroidal-peracyl- beta -glycosides that provides greater beta -anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).

公开(公告)号：EP0647235B1

公开(公告)日：1997-09-17

申请号：EP93911560.6

申请日：1993-04-02

申请人： PFIZER INC.

发明人： BUSCH, Frank, R. ,  GOGGIN, Kathleen, D. ,  LAMBERT, John, F. ,  SHINE, Russell, J. ,  WALINSKY, Stanley, W.

IPC分类号： C07J71/00 ,  C07J17/00

CPC分类号： C07J71/0005 ,  C07J17/005

摘要： A process for the synthesis of 1-O-steroidal-peracyl-β-glycosides that provides greater β-anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).