3-O-benzyl-1,2-O-isopropylidene l-sorbose | 1438263-44-5

• 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: 3-O-benzyl-1,2-O-isopropylidene l-sorbose
• 英文别名: (5S,7S,8R,9S)-7-(hydroxymethyl)-2,2-dimethyl-9-phenylmethoxy-1,3,6-trioxaspiro[4.4]nonan-8-ol
• CAS: 1438263-44-5
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: KUOHVPGJAWKPIK-FQLMCAECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene l-sorbose 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 生成 3,4,6-tri-O-benzyl-l-sorbose
  参考文献：
  名称：

  Stereoselective synthesis of (2S,3S,4R,5S)-3,4-dihydroxy-2,5-dihydroxymethyl pyrrolidine from l-sorbose

  摘要：

  One of the most frequently synthesized iminosugar derivatives is DMDP. Starting from L-sorbose, a practical method for the synthesis of derivatives of this five-membered iminocyclitol has been developed, involving straightforward steps and a convenient selective reduction of a ketoxime intermediate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.017
• 作为产物：
  描述：

  11,2:4,6-di-O-isopropylidene-α-L-sorbofuranose 在 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 反应 3.0h， 生成 3-O-benzyl-1,2-O-isopropylidene l-sorbose
  参考文献：
  名称：

  Stereoselective synthesis of (2S,3S,4R,5S)-3,4-dihydroxy-2,5-dihydroxymethyl pyrrolidine from l-sorbose

  摘要：

  One of the most frequently synthesized iminosugar derivatives is DMDP. Starting from L-sorbose, a practical method for the synthesis of derivatives of this five-membered iminocyclitol has been developed, involving straightforward steps and a convenient selective reduction of a ketoxime intermediate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.017

文献信息

• Stereoselective synthesis of (2S,3S,4R,5S)-3,4-dihydroxy-2,5-dihydroxymethyl pyrrolidine from l-sorbose
  作者：Sébastien Balieu、Arnaud Guilleret、Romain Reynaud、Agathe Martinez、Arnaud Haudrechy

  DOI：10.1016/j.carres.2013.03.017

  日期：2013.6

  One of the most frequently synthesized iminosugar derivatives is DMDP. Starting from L-sorbose, a practical method for the synthesis of derivatives of this five-membered iminocyclitol has been developed, involving straightforward steps and a convenient selective reduction of a ketoxime intermediate. (C) 2013 Elsevier Ltd. All rights reserved.