(3R,4R)-3-Hydroxy-4-trityloxymethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester | 743476-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3R,4R)-3-Hydroxy-4-trityloxymethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
• CAS: 743476-99-5
• 化学式: C₃₉H₃₅NO₄
• 分子量: 581.711
• InChiKey: IUELYKQEBLYXBD-XOAACPPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.24
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-Hydroxy-4-trityloxymethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 在 三乙胺 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 (3R,4R)-3-hydroxy-4-hydroxymethylpyrrolidine hydrochloride
  参考文献：
  名称：

  Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition

  摘要：

  Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoyleamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compound can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxy- methyl)pyrrolidin-3-ol and its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00367-6
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 (3R,4R)-4-(trityloxymethyl)pyrrolidin-3-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(3R,4R)-3-Hydroxy-4-trityloxymethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  The merits of bipartite transition-state mimics for inhibition of uracil DNA glycosylase

  摘要：

  The glycosidic bond hydrolysis reaction of the enzyme uracil DNA glycosylase (UDG) occurs by a two-step mechanism involving complete bond breakage to the uracil anion leaving group in the first step, formation of a discrete glycosyl cation-uracil anion intermediate, followed by water attack in a second transition-state leading to the enzyme-bound products of uracil and abasic DNA. We have synthesized and determined the binding affinities of unimolecular mimics of the substrate and first transition-state (TS1) in which the uracil base is covalently attached to the sugar, and in addition, bimolecular mimics of the second addition transition state (TS2) in which the base and sugar ate detached. We find that the bipartite mimics of TS2 are superior to the TS1 mimics. These results indicate that bipartite TS2 inhibitors could be useful for inhibition of glycosylases that proceed by stepwise reaction mechanisms. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.03.001