(3R,4S,5R,6S)-3,4,5,6-tetrahydroxyazepine | 212483-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (3R,4S,5R,6S)-3,4,5,6-tetrahydroxyazepine
• 英文别名: 3(S),4(R),5(S),6(R)-tetrahydroxyazepane；3(R),4(S),5(R),6(S)-tetrahydroxyazepane；1,6-Imino-1,6-didesoxy-D-galaktit；(3S,4R,5S,6R)-azepane-3,4,5,6-tetrol
• CAS: 212483-93-7
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: MRFFNLOQLBWKPJ-GUCUJZIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-azido-6-deoxy-D-galactopyranose 在 palladium on activated charcoal 氢气 作用下， 以 水 为溶剂， 反应 48.0h， 以90%的产率得到(3R,4S,5R,6S)-3,4,5,6-tetrahydroxyazepine
  参考文献：
  名称：

  七元亚氨基环醇的酶促/化学合成及生物学评价

  摘要：

  已经通过化学酶促或化学合成获得了几种多羟基全氢氮杂。(±)-3-叠氮基-2-羟基丙醛和磷酸二羟丙酮 (DHAP) 在 DHAP 依赖性醛缩酶存在下缩合，然后用酸性磷酸酶和异构酶处理得到 6-叠氮基-6-脱氧吡喃糖，其在还原胺化后得到标题化合物。亚氨基环醇也可以通过吡喃醛糖的化学操作获得，保护为苄基糖苷或二异丙叉基醚。因此，d-半乳糖产生内消旋 3,4,5,6-四羟基全氢氮杂，d-甘露糖产生具有 C2 对称轴的衍生物，N-乙酰氨基葡萄糖产生 6-乙酰氨基亚氨基环醇。通过化学方法进行内消旋氮杂糖的不对称化，得到 3-甲氧基-4,5,6-三羟基氮杂环庚烷。对这些氮杂糖的甲氧基衍生物的酶促合成尝试未成功，但导致了 1-脱氧-2-O-甲基甘露尻霉素的两种对映异构体。其中一些...

  DOI：

  10.1021/ja960975c

文献信息

• NOVEL LIPIDS AND COMPOSITIONS FOR THE DELIVERY OF THERAPEUTICS
  申请人：MANOHARAN Muthiah

  公开号：US20120095075A1

  公开（公告）日：2012-04-19

  The present invention provides lipids that are advantageously used in lipid particles for the in vivo delivery of therapeutic agents to cells. In particular, the invention provides lipids having the following structure:

  本发明提供了有利于用于体内向细胞传递治疗剂的脂质。具体而言，本发明提供具有以下结构的脂质：
• Chemo-enzymatic synthesis of polyhydroxyazepanes
  作者：Peter R. Andreana、Tom Sanders、Adam Janczuk、Joshua I. Warrick、Peng George Wang

  DOI：10.1016/s0040-4039(02)01465-x

  日期：2002.9

  Galactose oxidase (EC 1.1.3.9, GAO) is an extracellular copper-containing enzyme that utilizes molecular oxygen to convert the C6-primary hydroxyl Moiety Of D-galactopyranosides to hydrated aldehydes. Subsequent dehydratative Coupling with hydroxylamines produces oximes (3a-f), which, when subjected to conditions of hydrogenolysis, give rise to polyhydroxyazepanes (11-17). (C) 2002 Elsevier Science Ltd. All rights reserved.
• An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines
  作者：José Fuentes、Consolación Gasch、David Olano、M.Ángeles Pradera、Guillermo Repetto、Francisco J. Sayago

  DOI：10.1016/s0957-4166(02)00377-4

  日期：2002.8

  A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazelpines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropyranose derivatives. O- and N-Deprotection of the latter, followed by reduction with sodium cyanoborohydride, gives the target chiral iminocyclitols. The method is based on the capacity of the dialkoxycarbonylvinyl group to stabilize an amide ion, and the only limitation is the necessity for the starting glycosylenamine to have beta-D-configuration. The inhibitory activity of several intermediate iminocyclitols and aldopyranosylenamines on different alpha- and beta-glycosidases is also reported. (C) 2002 Published by Elsevier Science Ltd.
• Treatment of degenerative cartilage conditions in a mammal with Glycosidasc Inhibitors
  申请人：Ichikawa Yoshitaka

  公开号：US20070197471A1

  公开（公告）日：2007-08-23

  This invention relates to treating, preventing, and lessening the severity of conditions selected from the group consisting of osteoarthritis, rheumatoid arthritis, synovitis, subchondral bone edema, and cartilage degradation with administration of glycosidase inhibitors.
• US6462193B1
  申请人：——

  公开号：US6462193B1

  公开（公告）日：2002-10-08