(2R,3R,4R,5R)-1-benzyl-2-(hydroxymethyl)-4-phenylmethoxy-5-(phenylmethoxymethyl)pyrrolidin-3-ol | 1528732-02-6

• 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,3R,4R,5R)-1-benzyl-2-(hydroxymethyl)-4-phenylmethoxy-5-(phenylmethoxymethyl)pyrrolidin-3-ol
• CAS: 1528732-02-6
• 化学式: C₂₇H₃₁NO₄
• 分子量: 433.547
• InChiKey: NPNKRWIUUXWYLW-FPCALVHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-1-benzyl-2-(hydroxymethyl)-4-phenylmethoxy-5-(phenylmethoxymethyl)pyrrolidin-3-ol 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 钯 、 溶剂黄146 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以97%的产率得到Alpha-葡萄糖苷酶
  参考文献：
  名称：

  Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB

  摘要：

  A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from L-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-L-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular S(N)2-cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.068
• 作为产物：
  描述：

  L-xylopyranose 在 硫酸 、 四丁基碘化铵 、 sodium hydride 、 copper(II) sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 63.5h， 生成 (2R,3R,4R,5R)-1-benzyl-2-(hydroxymethyl)-4-phenylmethoxy-5-(phenylmethoxymethyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB

  摘要：

  A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from L-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-L-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular S(N)2-cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.068

文献信息

• Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB
  作者：Marc E. Bouillon、Stephen G. Pyne

  DOI：10.1016/j.tetlet.2013.11.068

  日期：2014.1

  A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from L-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-L-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular S(N)2-cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB. (C) 2013 Elsevier Ltd. All rights reserved.