SYNTHESIS, REACTIVITY STUDIES, AND X-RAY CRYSTAL-STRUCTURE OF (11R)-25-O-DEACETYL-11-DEOXO-11-HYDROXY-21,23-O-ISOPROPYLIDENERIFAMYCIN-S

被引：16

作者：

BARTOLUCCI, C

CELLAI, L

CERRINI, S

LAMBA, D

SEGRE, AL

BRIZZI, V

BRUFANI, M

机构：

[1] IST STRUTTURISTICA CHIM G GIACOMELLO,CNR,CP 10,I-00016 MONTEROTONDO,ITALY

[2] UNIV SIENA,DIPARTIMENTO FARMACOCHIMICOTECNOL,I-53100 SIENA,ITALY

[3] UNIV ROMA LA SAPIENZA,DIPARTIMENTO SCI BIOCHIM,I-00185 ROME,ITALY

来源：

HELVETICA CHIMICA ACTA | 1990年 / 73卷 / 01期

关键词：

D O I：

10.1002/hlca.19900730122

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The protected intermediate (11R)‐25‐O‐deacetyl‐11‐deoxo‐11‐hydroxy‐21,23‐O‐isopropylidenerifamycin S (7) has been synthesized starting from rifamicin S (2; Scheme 2), the former being a potential substrate for the preparation of new types of rifamicin‐S derivatives modified at C(11) and/or C(25). The reactivity of 7 toward acylations has been studied under both base‐ and acid‐catalyzed conditions. The compound either did not react or nr underwent unexpected reactions, and no acylation products could be isolated. The X‐ray crystal structure of 7 reveals that both OH groups at C(11) and C(25) are hindered, and this is probably the reason, why other take place faster than acylation. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：185 / 198

页数：14

共 16 条

[1]

[Anonymous], 1974, INT TABLES XRAY CRYS, VIV

[2] CHEMICAL MODIFICATIONS OF THE ALIPHATIC BRIDGE OF ANSAMYCINS - SYNTHESIS AND ACTIVITY OF 25-DEACETOXY-25-EPI-HYDROXYRIFAMYCIN-S [J].