Acetic acid (2S,3R,4S)-2-benzyl-4-iodo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-3-yl ester | 221341-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Acetic acid (2S,3R,4S)-2-benzyl-4-iodo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-3-yl ester
• 英文别名: [(2S,3R,4S)-2-benzyl-4-iodo-1-(9-phenylfluoren-9-yl)pyrrolidin-3-yl] acetate
• CAS: 221341-56-6
• 化学式: C₃₂H₂₈INO₂
• 分子量: 585.484
• InChiKey: UZROYGAYIJAOIA-CHQNGUEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S)-2-benzyl-4-iodo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-3-yl ester 在 silver tetrafluoroborate 、 lithium aluminium tetrahydride 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 生成 (2S,3R,4S)-2-Benzyl-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-3,4-diol
  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：

  (3S,4S)-5-Phenyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pent-1-en-3-ol 在 碘 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 Acetic acid (2S,3R,4S)-2-benzyl-4-iodo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-3-yl ester
  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

• 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。