[(2S)-1-[[(2R,3R,4R,5R)-5-(hexadecoxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]pyrrolidin-2-yl]methanol | 878675-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S)-1-[[(2R,3R,4R,5R)-5-(hexadecoxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]pyrrolidin-2-yl]methanol
• CAS: 878675-41-3
• 化学式: C₄₁H₆₅NO₅
• 分子量: 651.971
• InChiKey: IQQYHSMWEPBMOS-PODPKQJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  47
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S)-1-[[(2R,3R,4R,5R)-5-(hexadecoxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]pyrrolidin-2-yl]methanol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到(2R,3S,4S,5R)-2-Hexadecyloxymethyl-5-((S)-2-hydroxymethyl-pyrrolidin-1-ylmethyl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Hydrolytically stable arabinofuranoside analogs for the synthesis of arabinosyltransferase inhibitors

  摘要：

  The first members of two new families of arabinosyltransferase inhibitors, derived from previously reported hybrid compounds covalently associating all iminoalditol with an alpha-D-arabinofuranoside, have been prepared. In place of the arabinofuranoside moiety, they incorporate in their structure a Suitably Substituted tetrahydrofuran (C-glycoside family) or a cyclopentane (carba-sugar family) for mimicking the alpha-D-arabinofuranoside ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.029
• 作为产物：
  描述：

  2,5-脱水-D-甘露醇 在 草酰氯 、 sodium methylate 、 sodium hydride 、 sodium cyanoborohydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 [(2S)-1-[[(2R,3R,4R,5R)-5-(hexadecoxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]pyrrolidin-2-yl]methanol
  参考文献：
  名称：

  Hydrolytically stable arabinofuranoside analogs for the synthesis of arabinosyltransferase inhibitors

  摘要：

  The first members of two new families of arabinosyltransferase inhibitors, derived from previously reported hybrid compounds covalently associating all iminoalditol with an alpha-D-arabinofuranoside, have been prepared. In place of the arabinofuranoside moiety, they incorporate in their structure a Suitably Substituted tetrahydrofuran (C-glycoside family) or a cyclopentane (carba-sugar family) for mimicking the alpha-D-arabinofuranoside ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.029

文献信息

• Hydrolytically stable arabinofuranoside analogs for the synthesis of arabinosyltransferase inhibitors
  作者：Manon Chaumontet、Valérie Pons、Karine Marotte、Jacques Prandi

  DOI：10.1016/j.tetlet.2005.12.029

  日期：2006.2

  The first members of two new families of arabinosyltransferase inhibitors, derived from previously reported hybrid compounds covalently associating all iminoalditol with an alpha-D-arabinofuranoside, have been prepared. In place of the arabinofuranoside moiety, they incorporate in their structure a Suitably Substituted tetrahydrofuran (C-glycoside family) or a cyclopentane (carba-sugar family) for mimicking the alpha-D-arabinofuranoside ring. (c) 2005 Elsevier Ltd. All rights reserved.