N-((1R,2S,3R,4S,5R)-3-Hydroxy-2-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide | 475639-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: N-((1R,2S,3R,4S,5R)-3-Hydroxy-2-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide
• 英文别名: N-[(1R,2S,3R,4S,5R)-3-hydroxy-2-methoxy-6,8-dioxabicyclo[3.2.1]octan-4-yl]acetamide
• CAS: 475639-50-0
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: SJDUJBFHSRTVQJ-ANZWQOBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-((1R,2S,3R,4S,5R)-3-Hydroxy-2-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide 在 Lindlar catalyst 盐酸 、 sodium hydroxide 、 sodium azide 、 N-acetylneuraminic acid aldolase 、 Dowex 50W (H+) 、 硫酸 、 氢气 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-acetamido-4-guanidino-2,3,4,5-tetradeoxy-7-methoxy-D-glycero-D-galacto-non-2-enopyranosoic acid trifluoroacetic acid salt
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1
• 作为产物：
  描述：

  甲醇 、 2-acetamido-1,6:3,4-dianhydro-2-deoxy-β-D-talopyranose 在 Dowex 50W (H+) 作用下， 以95%的产率得到N-((1R,2S,3R,4S,5R)-3-Hydroxy-2-methoxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl)-acetamide
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1

文献信息

• Method for manufacturing neuraminic acid derivatives
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2360151A1

  公开（公告）日：2011-08-24

  Compounds represented by the formulae (I) and (13) and methods for manufacturing the compounds are provided: wherein R1 represents a C1-C19 alkyl group, R2 represents a C1-C4 alkyl group and Ac represents an acetyl group.

  提供了式 (I) 和 (13) 所代表的化合物以及制造这些化合物的方法： 其中 R1 代表 C1-C19 烷基，R2 代表 C1-C4 烷基，Ac 代表乙酰基。
• METHOD FOR MANUFACTURING NEURAMINIC ACID DERIVATIVES
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2132191B1

  公开（公告）日：2013-02-20
• US8455659B2
  申请人：——

  公开号：US8455659B2

  公开（公告）日：2013-06-04
• [EN] METHOD FOR MANUFACTURING NEURAMINIC ACID DERIVATIVES<br/>[FR] PROCÉDÉ DE FABRICATION DE DÉRIVÉS DE L'ACIDE NEURAMINIQUE
  申请人：DAIICHI SANKYO CO LTD

  公开号：WO2008126943A2

  公开（公告）日：2008-10-23

  [EN] A method for manufacturing neuraminic acid derivatives is provided, also synthetic intermediates of the neuraminic acid derivatives and methods for their manufacture, and neuraminic acid derivatives having high purity. [Means for solution] A synthetic intermediate compound represented by the formula (7) is provided: [wherein R3 represents alkyl; R4 and R5 each represents H, alkyl, phenyl, or together represent tetramethylene, pentamethylene, oxo].
  [FR] L'invention se rapporte à un procédé de fabrication de dérivés de l'acide neuraminique, à des intermédiaires synthétiques de l'acide neuraminique et à des procédés de fabrication de ces derniers, et à des dérivés de l'acide neuraminique de grande pureté. L'invention concerne un composé d'intermédiaire synthétique représenté par la formule (7) : [dans laquelle R³ représente alkyle; R⁴ et R⁵ représentent chacun H, alkyle, phényle, ou représentent ensemble tétraméthylène, pentaméthylène, oxo].
• Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives
  作者：Takeshi Honda、Takeshi Masuda、Shuku Yoshida、Masami Arai、Yoshiyuki Kobayashi、Makoto Yamashita

  DOI：10.1016/s0960-894x(02)00328-1

  日期：2002.8

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.