(2S,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane-3-carbonitrile | 350501-45-0

• 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: (2S,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane-3-carbonitrile
• CAS: 350501-45-0
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: XQKQZDQXBRKQKN-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane-3-carbonitrile 在 三乙基硼氢化锂 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 生成 [(3R,4S,5S)-4,5-Bis-benzyloxy-1-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-piperidin-3-yl]-methanol
  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：

  氰化四丁基铵 、 Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 以 甲苯 为溶剂， 以43%的产率得到(2S,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane-3-carbonitrile
  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

文献信息

• The rational design of an iminosugar inhibitor able to mimic substrate distortion occurring during retaining-cellulase hydrolysis
  作者：Sébastien Fort、Pedro M Coutinho、Martin Schülein、Robert Nardin、Sylvain Cottaz、Hugues Driguez

  DOI：10.1016/s0040-4039(01)00486-5

  日期：2001.5

  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.