(2S,3R,4R,5R)-1-benzyl-2-(hydroxymethyl)-4-phenylmethoxy-5-[tri(propan-2-yl)silyloxymethyl]pyrrolidin-3-ol | 1609168-88-8

• 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,4R,5R)-1-benzyl-2-(hydroxymethyl)-4-phenylmethoxy-5-[tri(propan-2-yl)silyloxymethyl]pyrrolidin-3-ol
• CAS: 1609168-88-8
• 化学式: C₂₉H₄₅NO₄Si
• 分子量: 499.766
• InChiKey: VUCHVJQTSQMNIM-AMSOURPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine 在 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine 、 (2S,3R,4R,5R)-1-benzyl-2-(hydroxymethyl)-4-phenylmethoxy-5-[tri(propan-2-yl)silyloxymethyl]pyrrolidin-3-ol
  参考文献：
  名称：

  Asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP]

  摘要：

  The asymmetric syntheses of 2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-D-glucitol [(+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with H2O gave the desired hydroxymethyl substituted pyrrolidine as a single diastereoisomer (>99:1 dr), with subsequent deprotection giving (+)-DGDP in good yield. Whereas in the case of (+)-ADGDP, displacement of iodide with NaN3 proved to be optimal, giving (+)-ADGDP in good yield after reduction and deprotection. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.100

文献信息

• Asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP]
  作者：Stephen G. Davies、Aude L.A. Figuccia、Ai M. Fletcher、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tet.2014.03.100

  日期：2014.6

  The asymmetric syntheses of 2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-D-glucitol [(+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with H2O gave the desired hydroxymethyl substituted pyrrolidine as a single diastereoisomer (>99:1 dr), with subsequent deprotection giving (+)-DGDP in good yield. Whereas in the case of (+)-ADGDP, displacement of iodide with NaN3 proved to be optimal, giving (+)-ADGDP in good yield after reduction and deprotection. (C) 2014 Elsevier Ltd. All rights reserved.