(1S)-1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanol | 302917-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S)-1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanol
• CAS: 302917-22-2
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: OSJRWERYMCTNBR-ZSYZGHEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanol 在 palladium on activated charcoal 甲醇 、 TEA 、 氢气 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 、 丙酮 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-hydroxy-1-((3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors

  摘要：

  Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50-50 mu M). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50=5 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00349-8
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 在 甲醇 、 sodium methylate 、 二正丁基氧化锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 生成 (1S)-1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanol
  参考文献：
  名称：

  Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors

  摘要：

  Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50-50 mu M). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50=5 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00349-8

文献信息

• Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors
  作者：C. Dini、P. Collette、N. Drochon、J.C. Guillot、G. Lemoine、P. Mauvais、J. Aszodi

  DOI：10.1016/s0960-894x(00)00349-8

  日期：2000.8

  Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50-50 mu M). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50=5 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.