A SIMPLE ONE POT SYNTHESIS OF AROMATIC STEROIDAL AND NONSTEROIDAL C-GLUCOSIDES VIA O-GLUCOSIDES

被引：3

作者：

ALLEVI, P

ANASTASIA, M

CIUFFREDA, P

SANVITO, AM

SCALA, A

机构：

[1] Department of Medical Chemistry and Biochemistry, Faculty of Medicine, University of Milan, 1-20133 Milan, Via Saldini

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 1992年 / 63卷 / 03期

关键词：

STEROIDAL C-GLUCOSIDES; C-GLUCOPYRANOSIDES; C-GLUCOSIDATION; STEROIDS; NAPHTHOLS;

D O I：

10.1016/0009-3084(92)90034-M

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Treatment of 2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl trifluoroacetate with an appropriate aromatic steroid under acid catalysis afforded first the O-glucopyranosides which subsequently rearranged to the corresponding C-glucopyranosides, useful for the synthesis of 2-beta-D-glucopyranosyl-3-hydroxy-1,3,5(10)-estratrien-17-one (1), or of 2-beta-D-glucopyranosyl-1,3,5(10)-estratriene-3,17beta-diol (2). The general applicability of the route was demonstrated by the synthesis of 1-beta-D-glucopyranosylnaphth-2-ol (3) and 2-beta-D-glucopyranosylnaphth-1-ol (4). Optimal conditions for regeneration of the hydroxy groups of the glucopyranosyl ring was also described. Unambiguous determination of the structure of all new compounds was obtained by means of H-1-NMR spectra at 500 MHz.

引用

页码：179 / 189

页数：11

共 8 条

[1] THE 1ST EXAMPLE OF C-GLUCOPYRANOSIDES [J].

ALLEVI, P ;

ANASTASIA, M ;

CIUFFREDA, P ;

FIECCHI, A ;

SCALA, A .

CHEMISTRY AND PHYSICS OF LIPIDS, 1990, 53 (2-3) :219-230

[2] THE 1ST TOTAL SYNTHESIS OF CARMINIC ACID [J].

ALLEVI, P ;

ANASTASIA, M ;

CIUFFREDA, P ;

FIECCHI, A ;

SCALA, A ;

BINGHAM, S ;

MUIR, M ;

TYMAN, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1319-1320

[3] A SIMPLE AND READY INTERNAL C-GLYCOSYLATION OF 2,3,5-TRI-O-BENZYLGLYCOFURANOSES PROMOTED BY THE BORON-TRIFLUORIDE DIETHYL-ETHER COMPLEX [J].

ANASTASIA, M ;

ALLEVI, P ;

CIUFFREDA, P ;

FIECCHI, A ;

SCALA, A .

CARBOHYDRATE RESEARCH, 1990, 208 :264-266

[4] CLEAVAGE OF ETHERS [J].

BHATT, MV ;

KULKARNI, SU .

SYNTHESIS-STUTTGART, 1983, (04) :249-282

[5] ASSIGNMENT OF THE BETA-CONFIGURATION TO THE C-GLYCOSYL BOND IN CARMINIC ACID [J].

FIECCHI, A ;

ANASTASIA, M ;

GALLI, G ;

GARIBOLDI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1511-1511

[6] NUCLEAR MAGNETIC RESONANCE SPECTRA AND STRUCTURES OF SOME C-GLYCOSYLFLAVONOIDS [J].

HILLIS, WE ;

HORN, DHS .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (04) :531-&

[7] SYNTHESIS OF C-GLYCOSYLARENES BY WAY OF INTERNAL REACTIONS OF BENZYLATED AND BENZOYLATED CARBOHYDRATE-DERIVATIVES [J].

MARTIN, OR ;

HENDRICKS, CAV ;

DESHPANDE, PP ;

CUTLER, AB ;

KANE, SA ;

RAO, SP .

CARBOHYDRATE RESEARCH, 1990, 196 :41-58

[8] SYNTHETIC STUDY TOWARD VINEOMYCINS - SYNTHESIS OF C-ARYL GLYCOSIDE SECTOR VIA CP2HFCL2-AGCLO4-PROMOTED TACTICS [J].

MATSUMOTO, T ;

KATSUKI, M ;

JONA, H ;

SUZUKI, K .

TETRAHEDRON LETTERS, 1989, 30 (45) :6185-6188

← 1 →