PRACTICAL SYNTHESIS OF A C-GLYCOSYL FLAVONOID VIA O-]C GLYCOSIDE REARRANGEMENT

被引：18

作者：

KUMAZAWA, T ^{[1
]}

OHKI, K ^{[1
]}

ISHIDA, M ^{[1
]}

SATO, S ^{[1
]}

ONODERA, JI ^{[1
]}

MATSUBA, S ^{[1
]}

机构：

[1] YAMAGATA UNIV, FAC ENGN, DEPT MAT SCI & ENGN, YONEZAWA, YAMAGATA 992, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 05期

关键词：

D O I：

10.1246/bcsj.68.1379

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The C-glycosylation of 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the beta-C-glucoside in a good yield via O-->C glycoside rearrangement. Subsequently, aldol condensation of the C-glucoside with benzaldehyde afforded the corresponding beta-C glucosyl chalcone in a good yield.

引用

页码：1379 / 1384

页数：6

共 22 条

[1] CATARTE BK, 1991, TETRAHEDRON, V47, P1815
[2] CHOPIN J, 1988, ADV RES 1980, P63
[3] FRICK W, 1989, LIEBIGS ANN CHEM, P565
[4] SIMPLE SYNTHESIS OF GLYCOSYL FLUORIDES
HAYASHI, M
HASHIMOTO, S
NOYORI, R
[J]. CHEMISTRY LETTERS, 1984, (10) : 1747 - 1750
[5] HAYASHI Y, 1987, MOKUZAI GAKKAISHI, V33, P511
[6] CHEMISTRY OF EUCALYPT KINOS .4. EUCALYPTUS HEMIPHLOIA KINO
HILLIS, WE
CARLE, A
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1963, 16 (01) : 147 - &
[7] POLYPHENOLS OF NOTHOFAGUS SPECIES .2. HEARTWOOD OF NOTHOFAGUS FUSCA
HILLIS, WE
INOUE, T
[J]. PHYTOCHEMISTRY, 1967, 6 (01) : 59 - +
[8] JARAMILLO C, 1994, SYNTHESIS STUTTGART, V1, P1
[9] JAY M, 1993, ADV RES SINCE 1986, P57
[10] KOMETANI T, 1988, SYNTHESIS-STUTTGART, P1005

← 1 2 3 →