(1R,2R,3R,5S,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine | 394706-29-7

• 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,5S,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine
• 英文别名: tert-butyl-[[(1R,2R,3R,5S,8S)-5-methyl-1,2-bis(phenylmethoxy)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-3-yl]methoxy]-diphenylsilane
• CAS: 394706-29-7
• 化学式: C₃₉H₄₇NO₃Si
• 分子量: 605.893
• InChiKey: AFRFMYBBEJAOLE-KLEPPPRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 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,5S,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以85%的产率得到(1R,2R,3R,5S,7aS)-1,2-dibenzyloxy-3-hydroxymethyl-5-methylpyrrolizidine
  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：

  [(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]carbaldehyde 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 (1R,2R,3R,5S,7aS)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine
  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