(2S,3S,4S)-2-benzyl-3,4-dihydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine | 737805-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3S,4S)-2-benzyl-3,4-dihydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine
• 英文别名: (2S,3S,4S)-2-benzyl-1-(9-phenylfluoren-9-yl)pyrrolidine-3,4-diol
• CAS: 737805-75-3
• 化学式: C₃₀H₂₇NO₂
• 分子量: 433.55
• InChiKey: KQVMVJQTHMSRAN-AWCRTANDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-benzyl-3,4-dihydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2S,3S,4S)-2-苄基吡咯烷-3,4-二醇
  参考文献：
  名称：

  α-Rhamnosidase inhibitory activities of polyhydroxylated pyrrolidine

  摘要：

  We designed and synthesized polyhydroxylated pyrrolidines 1-12 from L-tyrosine, L-phenylalanine, and D-tyrosine through iodine-mediated intramolecular cyclization followed by Woodward-Prevost reaction. The synthetic polyhydroxylated pyrrolidines were identified with structure-based inhibitory activity and selective inhibitory activity against alpha-rhamnosidase. (2S,3S,4R)-deacetyl anisomycin 7 was the best inhibitor among the 12 polyhydroxylated pyrrolidines because it possesses the same stereoconfiguration at C1, C2, C3 as alpha-L-rhamnopyranoside. An investigation into the nature of the inhibition showed that the synthetic pyrrolidines are competitive inhibitors. They also did not have remarkable inhibitory activity against seven glycosidases (alpha-glucosidase, alpha-mannosidase, alpha-amylase, beta-glucosidase, beta-galactosidase, beta-amylase, and invertase). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.051
• 作为产物：
  描述：

  (2S,3S,4S)-3-acetoxy-2-benzyl-4-iodo-N-(9-phenylfluoren-9-yl)pyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (2S,3S,4S)-2-benzyl-3,4-dihydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine
  参考文献：
  名称：

  α-Rhamnosidase inhibitory activities of polyhydroxylated pyrrolidine

  摘要：

  We designed and synthesized polyhydroxylated pyrrolidines 1-12 from L-tyrosine, L-phenylalanine, and D-tyrosine through iodine-mediated intramolecular cyclization followed by Woodward-Prevost reaction. The synthetic polyhydroxylated pyrrolidines were identified with structure-based inhibitory activity and selective inhibitory activity against alpha-rhamnosidase. (2S,3S,4R)-deacetyl anisomycin 7 was the best inhibitor among the 12 polyhydroxylated pyrrolidines because it possesses the same stereoconfiguration at C1, C2, C3 as alpha-L-rhamnopyranoside. An investigation into the nature of the inhibition showed that the synthetic pyrrolidines are competitive inhibitors. They also did not have remarkable inhibitory activity against seven glycosidases (alpha-glucosidase, alpha-mannosidase, alpha-amylase, beta-glucosidase, beta-galactosidase, beta-amylase, and invertase). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.051

文献信息

• Stereodivergent and Regioselective Synthesis of 3,4-<i>cis</i>- and 3,4-<i>trans</i>-Pyrrolidinediols from α-Amino Acids
  作者：Jin Hyo Kim、Marcus J. C. Long、Jun Young Kim、Ki Hun Park

  DOI：10.1021/ol049237g

  日期：2004.6.1

  [reaction: see text] Highly stereodivergent Woodward-Prevost reaction applied to iodoacetates derived from homochiral alpha-amino acids afforded enantiopure 3,4-cis- and 3,4-trans-pyrrolidinediol derivatives, with control over the protecting group, allowing for differential protection.

  [反应：见正文]对衍生自同手性α-氨基酸的碘乙酸酯进行高度立体发散的伍德沃德-普雷沃斯特反应，得到对映体纯的3,4-顺式和3,4-反式吡咯烷二醇衍生物，控制了保护基，从而可以区分保护。