(2S,3S,4S)-2-苄基吡咯烷-3,4-二醇 | 502843-88-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (2S,3S,4S)-2-苄基吡咯烷-3,4-二醇
• 英文名称: 3,4-Pyrrolidinediol, 2-(phenylmethyl)-, (2S,3S,4S)-
• 英文别名: (2S,3S,4S)-2-benzylpyrrolidine-3,4-diol
• CAS: 502843-88-1
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: QJEAQFLWGBHQQE-DCAQKATOSA-N

物化性质

• 沸点：
  350.6±37.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3S,4S)-3-acetoxy-2-benzyl-4-iodo-N-(9-phenylfluoren-9-yl)pyrrolidine 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 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

文献信息

• Synthesis of pyrrolidine based natural or unnatural product derivatives (1): Application of efficient asymmetric induction of C‐2 position in polysubstituted pyrrolidines
  作者：Hyung Jae Jeong、Ju Man Lee、Min Kyu Kim、Sang‐Gyeong Lee

  DOI：10.1002/jhet.5570390525

  日期：2002.9

  A novel method for synthesis of polysubstituted pyrrolidines, which possess a C-2 stereocenter, was developed. The strategy involves Grignard addition to the succinimide, derived from L-tartaric acid, followed by stereocontrolled triethylsilane promoted reduction of the resulting cyclic amidols.

  开发了一种新的合成具有C-2立体中心的多取代吡咯烷的方法。该策略涉及将格利雅（Grignard）加入到衍生自L-酒石酸的琥珀酰亚胺中，然后通过立体控制的三乙基硅烷促进还原所得的环状酰胺。
• Synthesis of Nitrone‐derived Pyrrolidine Scaffolds and Their Combinatorial Libraries to Develop Selective α‐ <scp>l</scp> ‐Rhamnosidase Inhibitors
  作者：Wei‐An Chen、Huang‐Yi Li、Ashik Sayyad、Chun‐Yen Huang、Wei‐Chieh Cheng

  DOI：10.1002/asia.202200172

  日期：2022.7.15

  efficient strategy to develop selective α-l-rhamnosidase inhibitors is described. Five functionalized pyrrolidine scaffolds were rationally designed and synthesized from cyclic nitrones. Their corresponding diverse libraries prepared by combinatorial chemistry enable us to increase the chemical space of pyrrolidine-based iminosugars and allow us to identify selective and potent α-l-rhamnosidase inhibitors

  描述了开发选择性α- l-鼠李糖苷酶抑制剂的有效策略。以环状硝酮为原料，合理设计并合成了五种功能化吡咯烷支架。通过组合化学制备的相应的多样化文库使我们能够增加基于吡咯烷的亚胺糖的化学空间，并使我们能够鉴定选择性且有效的α- l-鼠李糖苷酶抑制剂。
• NATURAL COMPOUNDS AND FIBROSIS
  申请人：MEDIZINISCHE HOCHSCHULE HANNOVER (MHH)

  公开号：US20190350923A1

  公开（公告）日：2019-11-21

  The present invention relates to an inhibitor of miR-671-5p for use in a method of preventing or treating fibrosis. Further, the present invention encompasses a kit comprising said inhibitor of miR-671-5p. The present invention also relates to an in vitro method for identifying a compound for preventing or treating fibrosis.
• α-Rhamnosidase inhibitory activities of polyhydroxylated pyrrolidine
  作者：Jin Hyo Kim、Marcus J. Curtis-Long、Woo Duck Seo、Jin Hwan Lee、Byong Won Lee、Yong Jin Yoon、Kyu Young Kang、Ki Hun Park

  DOI：10.1016/j.bmcl.2005.06.051

  日期：2005.10

  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.