(1R)-1-C-hexyl-1,5-dideoxy-1,5-imino-D-xylitol | 1309458-93-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (1R)-1-C-hexyl-1,5-dideoxy-1,5-imino-D-xylitol
• 英文别名: α-1-C-hexyl-1,5-dideoxy-1,5-imino-D-xylitol；(2R,3S,4S,5R)-2-hexylpiperidine-3,4,5-triol
• CAS: 1309458-93-2
• 化学式: C₁₁H₂₃NO₃
• 分子量: 217.309
• InChiKey: JVCIUBNETYXXOR-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1R)-2,3,4-tri-O-benzyl-N-(benzyloxy)carbonyl-1-C-hex-2-enyl-1,5-dideoxy-1,5-imino-D-xylitol 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 水 、 异丙醇 为溶剂， 反应 22.0h， 以100%的产率得到(1R)-1-C-hexyl-1,5-dideoxy-1,5-imino-D-xylitol
  参考文献：
  名称：

  一种合成1- C-烯丙基亚氨基亚木糖醇和-1-阿拉伯糖醇及其快速功能化的改进方法

  摘要：

  作为我们致力于设计和合成新的亚氨基糖作为溶酶体贮积症的药理分子伴侣的研究计划的一部分，我们开发了一种快速有效的方法，可从中获得功能化和非功能化的1- C烷基化衍生物。d - xylo和l - arabino系列。这些化合物，如葡萄糖和半乳糖模拟物，被设计成分别是与高雪氏病有关的β-葡萄糖脑苷脂酶和负责Krabbe病的β-半乳糖脑苷脂酶的有效抑制剂。合成的关键步骤是将烯丙基三甲基硅烷非对映选择性地加到d-低聚木糖或升-阿拉伯ñ -苄氧保护glycopyranosylamine。该保护基允许使用复分解或氧化反应将获得的亚氨基糖直接官能化。为了确定二羟基化反应产物的绝对构型，成功地使用了电子圆二色性光谱法的原位二钼法。

  DOI：

  10.1016/j.tet.2012.12.082

文献信息

• Compounds for their use as drugs for the treatment and/or the prevention of infection(s) caused by biofilm-forming bacteria
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US10745395B2

  公开（公告）日：2020-08-18

  The present invention relates to compounds of the following formula (I), wherein: m represents an integer being equal to 0, 1, 2, 3, 4, 5 or 6, X represents a simple bond or a radical —CHR1 wherein R1 represents:—a hydrogen atom, or—a linear or branched, possibly interrupted by up to 3 heteroatoms selected from O, S or N and/or possibly substituted, (C1-C12)-alkyl, R2, R3 and R4 represent independently from each other:—a hydrogen atom, or—a linear or branched (C1-C12-alkyl or (C1-C12)-acyl R5 represents:—a hydrogen atom, or—a linear or branched, possibly substituted, (C1-C13)-alkyi possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, R6 represents:—a hydrogen atom, or—a linear or branched possibly substituted (C1-C12)-alkyl, possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, for their use as antibacterial drugs for the treatment and/or the prevention of infection(s) caused by biofilm-forming bacteria.

  本发明涉及下式（I）的化合物，其中：m 代表等于 0、1、2、3、4、5 或 6 的整数，X 代表单键或自由基-CHR1，其中 R1 代表：氢原子，或直链或支链的、可能被最多 3 个选自 O、S 或 N 的杂原子间断的和/或可能被取代的 (C1-C12)- 烷基，R2、R3 和 R4 相互独立地代表：氢原子，或直链或支链的 (C1-C12) - 烷基或 (C1-C12)- 芳基 R5 代表：氢原子，或直链或支链的 (C1-C12)- 烷基或 (C1-C12)- 芳基-氢原子，或直链或支链、可能被取代的（C1-C13）烷基，可能被最多 3 个选自 O、S 或 N 的杂原子取代和间断，R6 代表：氢原子，或直链或支链、可能被取代的（C1-C12）烷基，可能被最多 3 个选自 O、S 或 N 的杂原子取代和间断，用作抗菌药物，用于治疗和/或预防由生物膜形成细菌引起的感染。
• 1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity
  作者：Farah Oulaïdi、Estelle Gallienne、Philippe Compain、Olivier R. Martin

  DOI：10.1016/j.tetasy.2011.02.024

  日期：2011.3

  The stereoselective synthesis of 1-C-alkyl iminosugars in the D-xylo and L-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center. (C) 2011 Elsevier Ltd. All rights reserved.
• COMPOUNDS FOR THEIR USE AS DRUGS FOR THE TREATMENT AND/OR THE PREVENTION OF INFECTION(S) CAUSED BY BIOFILM-FORMING BACTERIA
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20180030047A1

  公开（公告）日：2018-02-01

  Disclosed are compounds of the following formula I: wherein: m represents an integer being equal to 0, 1, 2, 3, 4, 5 or 6, X represents a simple bond or a radical —CHR 1 — wherein R 1 represents: a hydrogen atom, or a linear or branched, possibly interrupted by up to 3 heteroatoms selected from O, S or N and/or possibly substituted, (C 1 -C 12 )-alkyl, R 2 , R 3 and R 4 represent independently from each other: a hydrogen atom, or a linear or branched (C 1 -C 12 )-alkyl or (C 1 -C 12 )-acyl R 5 represents: a hydrogen atom, or a linear or branched, possibly substituted, (C 1 -C 13 )-alkyl possibly interrupted by up to 3 heteroatoms selected from O, S or N, R 6 represents: a hydrogen atom, or a linear or branched possibly substituted (C 1 -C 12 )-alkyl, possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, for their use as antibacterial drugs.
• An improved methodology for the synthesis of 1-C-allyl imino-d-xylitol and -l-arabinitol and their rapid functionalization
  作者：Anna Biela、Farah Oulaïdi、Estelle Gallienne、Marcin Górecki、Jadwiga Frelek、Olivier R. Martin

  DOI：10.1016/j.tet.2012.12.082

  日期：2013.4

  As part of our research program dedicated to the design and synthesis of new iminosugars as pharmacological chaperones for the treatment of lysosomal storage disorders, we developed a rapid and efficient methodology for the access to functionalized and non-functionalized 1-C-alkylated derivatives in the d-xylo and l-arabino series. These compounds, as gluco and galacto mimics, were designed to be potent

  作为我们致力于设计和合成新的亚氨基糖作为溶酶体贮积症的药理分子伴侣的研究计划的一部分，我们开发了一种快速有效的方法，可从中获得功能化和非功能化的1- C烷基化衍生物。d - xylo和l - arabino系列。这些化合物，如葡萄糖和半乳糖模拟物，被设计成分别是与高雪氏病有关的β-葡萄糖脑苷脂酶和负责Krabbe病的β-半乳糖脑苷脂酶的有效抑制剂。合成的关键步骤是将烯丙基三甲基硅烷非对映选择性地加到d-低聚木糖或升-阿拉伯ñ -苄氧保护glycopyranosylamine。该保护基允许使用复分解或氧化反应将获得的亚氨基糖直接官能化。为了确定二羟基化反应产物的绝对构型，成功地使用了电子圆二色性光谱法的原位二钼法。