(R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester | 286458-65-9

• 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: (R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester
• CAS: 286458-65-9
• 化学式: C₂₆H₂₈O₅
• 分子量: 420.505
• InChiKey: IDVKNUACUWUUCV-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 四丙基高钌酸铵 、 copper(I) bromide dimethylsulfide complex 、 L-(+)-酒石酸二异丙酯 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 (2S,3R,4R)-5-[bis(4-methoxyphenyl)-phenylmethoxy]-2-ethenyl-4-methylpentane-1,3-diol
  参考文献：
  名称：

  Stereoselective synthesis of a fully protected C13–C23 fragment of tedanolide

  摘要：

  The combination of a high-yielding dienyllithium addition and a highly diastereoselective 1,2-reduction allows the preparation of the completely protected C-13-C-23 fragment 3 of the potent cytotoxic agent tedanolide 1. A convergent approach was used, namely a late stage coupling of the dienyllithium 16 with the selectively protected aldehyde 5 followed by oxidation-reduction and final epoxidation to give 3. The dienylstannane 4 was prepared from the dibromide 6 in five steps, the key step being the highly regio-and stereoselective stannylcupration of the alkyne 7. The commercially available hydroxy ester 10 was converted in 11 steps to the aldehyde 5. The compound 3 could potentially be a key intermediate for the synthesis of tedanolide 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.024
• 作为产物：
  描述：

  (-)-甲基-D-BATA-羟基异丁酸酯 、 4,4'-双甲氧基三苯甲基氯 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of a fully protected C13–C23 fragment of tedanolide

  摘要：

  The combination of a high-yielding dienyllithium addition and a highly diastereoselective 1,2-reduction allows the preparation of the completely protected C-13-C-23 fragment 3 of the potent cytotoxic agent tedanolide 1. A convergent approach was used, namely a late stage coupling of the dienyllithium 16 with the selectively protected aldehyde 5 followed by oxidation-reduction and final epoxidation to give 3. The dienylstannane 4 was prepared from the dibromide 6 in five steps, the key step being the highly regio-and stereoselective stannylcupration of the alkyne 7. The commercially available hydroxy ester 10 was converted in 11 steps to the aldehyde 5. The compound 3 could potentially be a key intermediate for the synthesis of tedanolide 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.024

文献信息

• Unexpected Preference of the <i>E. coli</i> Translation System for the Ester Bond during Incorporation of Backbone-Elongated Substrates
  作者：Shinsuke Sando、Kenji Abe、Nobuhiko Sato、Toshihiro Shibata、Keigo Mizusawa、Yasuhiro Aoyama

  DOI：10.1021/ja068033n

  日期：2007.5.1

  There have been recent advances in the ribosomal synthesis of various molecules composed of nonnatural ribosomal substrates. However, the ribosome has strict limitations on substrates with elongated backbones. Here, we show an unexpected loophole in the E. coli translation system, based on a remarkable disparity in its selectivity for beta-amino/hydroxy acids. We challenged beta-hydroxypropionic acid (beta-HPA), which is less nucleophilic than beta-amino acids but free from protonation, to produce a new repertoire of ribosome-compatible but main-chain-elongated substrates. PAGE analysis and mass-coupled S-tag assays of amber suppression experiments using yeast suppressor tRNA(CUA)(Phe) confirmed the actual incorporation of beta-HPA into proteins/oligopeptides. We investigated the side-chain effects of beta-HPA and found that the side chain at position alpha and R stereochemistry of the beta-substrate is preferred and even notably enhances the efficiency of incorporation as compared to the parent substrate. These results indicate that the E. coli translation machinery can utilize main-chain-elongated substrates if the pK(a) of the substrate is appropriately chosen.
• Efficient Synthesis of the C₁−C₁₁ Fragment of the Tedanolides. The Nonaldol Aldol Process in Synthesis
  作者：Michael E. Jung、Rodolfo Marquez

  DOI：10.1021/ol005675l

  日期：2000.6.1

  [GRAPHICS]The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C-1-C-11 fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.