(1R,2R,3R,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethylpyrrolizidine | 291510-06-0

• 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: (1R,2R,3R,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethylpyrrolizidine
• 英文别名: [(1R,2R,3R,8S)-1,2-bis(phenylmethoxy)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-3-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 291510-06-0
• 化学式: C₃₈H₄₅NO₃Si
• 分子量: 591.866
• InChiKey: JLKYTOYXBFVCPO-UPIAJAFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethylpyrrolizidine 在 palladium on activated charcoal 盐酸 、 Amberlite IRA-400 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 (1R,2R,3R,7aS)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine
  参考文献：
  名称：

  Polyhydroxylated pyrrolizidines. Part I: Short and highly stereocontrolled syntheses of hyacinthacines

  摘要：

  Two short and highly stereocontrolled syntheses for 7a-epi-hyacinthacine A(2) (7-deoxyalexine) 3 and 5,7a-diepihyacinthacine A(3) 4 are, respectively, reported herein. An appropriately protected polyhydroxypyrrolidine. (2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 5, readily available from D-fructose, was chosen as the chiral starting material. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00440-2
• 作为产物：
  描述：

  (E)-3-[(2'S,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propenal 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以45%的产率得到(1R,2R,3R,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethylpyrrolizidine
  参考文献：
  名称：

  Polyhydroxylated pyrrolizidines. Part I: Short and highly stereocontrolled syntheses of hyacinthacines

  摘要：

  Two short and highly stereocontrolled syntheses for 7a-epi-hyacinthacine A(2) (7-deoxyalexine) 3 and 5,7a-diepihyacinthacine A(3) 4 are, respectively, reported herein. An appropriately protected polyhydroxypyrrolidine. (2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 5, readily available from D-fructose, was chosen as the chiral starting material. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00440-2

文献信息

• Polyhydroxylated pyrrolizidines. Part I: Short and highly stereocontrolled syntheses of hyacinthacines
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Rafael Robles、Francisco Franco

  DOI：10.1016/s0957-4166(01)00440-2

  日期：2001.9

  Two short and highly stereocontrolled syntheses for 7a-epi-hyacinthacine A(2) (7-deoxyalexine) 3 and 5,7a-diepihyacinthacine A(3) 4 are, respectively, reported herein. An appropriately protected polyhydroxypyrrolidine. (2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 5, readily available from D-fructose, was chosen as the chiral starting material. (C) 2001 Elsevier Science Ltd. All rights reserved.