公开(公告)号：DE59105210D1

公开(公告)日：1995-05-24

申请号：DE59105210

申请日：1991-01-23

Applicant: BASF AG

Inventor： VON DEESSEN ULRICH DR ,  PAUST JOACHIM DR ,  KAISER KLAUS DR ,  INDEST HELMUT DR

IPC: C07H15/18 ,  C07H15/10 ,  C07H15/26

Abstract: (A) 4-Glycopyranosyloxy-2-methyl -2-buten-1-al derivs. of formula (IVa) and (Va) are new: R4 = CH2OAc or COOMe; Ac = acetyl. (B) Prodn. of retinyl glycosides of formula (I) is effected by (a) reacting an acylated glycoside deriv. of formula (II) with a 4-hydroxy-2-methyl-2 -buten-1-al acetal of formula (III); (b) treating the prod. (IV) with an acid, (c) reacting the resulting aldehdye (V) with a beta-ionylidene -ethyl-triphenyl phosphonium salt of formula (VI) under Wittig conditions; and (d) removing the acyl gps. from the prod.: Z= a linear or branched glycoside gp. comprising 1-20 glycoxide units; Z'=Z in which all OH gps. are replaced by OCOR1; R1 = 1-10C alkyl or aralkyl, R2 and R3 = 1-10C alkyl or 7-10C aralkyl, or R2+R3 = ethylene or propylene opt. substd. by 1-4C alkyl; Y = a leaving gp.; X = a monovalent anion. (C) The use of cpds. (IV) and (V) for prodn. of medicaments is also new.

公开(公告)号：DE4003094A1

公开(公告)日：1991-08-08

申请号：DE4003094

申请日：1990-02-02

Applicant: BASF AG

Inventor： DEESSEN ULRICH VON DR ,  PAUST JOACHIM DR ,  KAISER KLAUS DR ,  INDEST HELMUT DR

IPC: C07H15/18 ,  C07H15/10 ,  C07H15/26

Abstract: (A) 4-Glycopyranosyloxy-2-methyl -2-buten-1-al derivs. of formula (IVa) and (Va) are new: R4 = CH2OAc or COOMe; Ac = acetyl. (B) Prodn. of retinyl glycosides of formula (I) is effected by (a) reacting an acylated glycoside deriv. of formula (II) with a 4-hydroxy-2-methyl-2 -buten-1-al acetal of formula (III); (b) treating the prod. (IV) with an acid, (c) reacting the resulting aldehdye (V) with a beta-ionylidene -ethyl-triphenyl phosphonium salt of formula (VI) under Wittig conditions; and (d) removing the acyl gps. from the prod.: Z= a linear or branched glycoside gp. comprising 1-20 glycoxide units; Z'=Z in which all OH gps. are replaced by OCOR1; R1 = 1-10C alkyl or aralkyl, R2 and R3 = 1-10C alkyl or 7-10C aralkyl, or R2+R3 = ethylene or propylene opt. substd. by 1-4C alkyl; Y = a leaving gp.; X = a monovalent anion. (C) The use of cpds. (IV) and (V) for prodn. of medicaments is also new.