(2R,3S,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-pentanedial | 350501-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-pentanedial
• 英文别名: (2R,3S,4R)-2-(hydroxymethyl)-3,4-bis(phenylmethoxy)pentanedial
• CAS: 350501-47-2
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: HITPXVGLNYEMHT-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-pentanedial 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (3S,4S,5R)-1-((2S,3S,4S,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-hydroxymethyl-piperidine-3,4-diol
  参考文献：
  名称：

  The rational design of an iminosugar inhibitor able to mimic substrate distortion occurring during retaining-cellulase hydrolysis

  摘要：

  This paper reports the rational design, synthesis and biochemical evaluation of a new type of cellulase inhibitor. This isofagomine isomer analogous to the beta -L-idopyranose linked to a glucosidic unit by a methylenic bond is able to mimic the pseudo-axial orientation of the 'aglycon' observed in the X-ray structure of a non-hydrolyzable thiooligosaccharide/cellulase complex. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00486-5
• 作为产物：
  描述：

  [(2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl]-methanol 在 硫酸 sodium periodate 、 乙酸酐 作用下， 以 甲醇 、 水 为溶剂， 生成 (2R,3S,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-pentanedial
  参考文献：
  名称：

  The rational design of an iminosugar inhibitor able to mimic substrate distortion occurring during retaining-cellulase hydrolysis

  摘要：

  This paper reports the rational design, synthesis and biochemical evaluation of a new type of cellulase inhibitor. This isofagomine isomer analogous to the beta -L-idopyranose linked to a glucosidic unit by a methylenic bond is able to mimic the pseudo-axial orientation of the 'aglycon' observed in the X-ray structure of a non-hydrolyzable thiooligosaccharide/cellulase complex. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00486-5