[(3R,4S)-5-phenyl-4-[(9-phenylfluoren-9-yl)amino]pent-1-en-3-yl] acetate | 221341-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(3R,4S)-5-phenyl-4-[(9-phenylfluoren-9-yl)amino]pent-1-en-3-yl] acetate
• CAS: 221341-48-6
• 化学式: C₃₂H₂₉NO₂
• 分子量: 459.588
• InChiKey: WYYPNKOODRIASD-IOWSJCHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3R,4S)-5-phenyl-4-[(9-phenylfluoren-9-yl)amino]pent-1-en-3-yl] acetate 在 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 生成
  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：

  在 (S)-BINAL 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(3R,4S)-5-phenyl-4-[(9-phenylfluoren-9-yl)amino]pent-1-en-3-yl] acetate
  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。
• Diastereoselective iodoamidation of 3-acetyloxybut-1-enylamines: simple synthesis of a precursor of aza sugars involving a pyrrolidine ring
  作者：Woo Song Lee、Ki Chang Jang、Jin Hyo Kim、Ki Hun Park

  DOI：10.1039/a809083a

  日期：——

  3-Acetyloxybut-1-enylamines 3–9 were easily transformed using iodine to pyrrolidine derivatives 3a–9a, precursors for aza sugars, via a diastereoselective iodoamidation.

  3-乙酰氧基-1-丁烯胺3-9很容易通过碘代酰胺化反应转化为吡咯烷衍生物3a-9a，后者是氮杂糖的前体。