[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]carbaldehyde | 394706-11-7

• 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: [(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]carbaldehyde
• 英文别名: benzyl (2R,3R,4R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-formyl-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
• CAS: 394706-11-7
• 化学式: C₄₄H₄₇NO₆Si
• 分子量: 713.946
• InChiKey: MZKSRQWHQYIUQG-CVGILMMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 68.0h， 生成 (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：

  (2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 在 四丙基高钌酸铵 、 4 Angstroem MS 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]carbaldehyde
  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