(+)-(2R)-1-fluoro-3-(triphenylmethoxy)propan-2-ol | 142631-77-4

• 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: (+)-(2R)-1-fluoro-3-(triphenylmethoxy)propan-2-ol
• 英文别名: (R)-1-fluoro-3-(trityloxy)propan-2-ol；(2R)-1-fluoro-3-trityloxypropan-2-ol
• CAS: 142631-77-4
• 化学式: C₂₂H₂₁FO₂
• 分子量: 336.406
• InChiKey: GEJLOZOSEYLIMR-NRFANRHFSA-N

物化性质

• 熔点：
  70.6 °C
• 沸点：
  468.0±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙烯基磷酸二乙酯 、 (+)-(2R)-1-fluoro-3-(triphenylmethoxy)propan-2-ol 在 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.25h， 以37%的产率得到diethyl (R)-(2-(1-fluoro-3-(trityloxy)propan-2-yloxy)ethyl)phosphonate
  参考文献：
  名称：

  The effect of novel [3-fluoro-(2-phosphonoethoxy)propyl]purines on the inhibition of Plasmodium falciparum, Plasmodium vivax and human hypoxanthine–guanine–(xanthine) phosphoribosyltransferases

  摘要：

  Protozoan parasites from the Plasmodiidae family are the causative agents of malaria. Inhibition of hypoxanthine guanine-(xanthine) phosphoribosyltransferase (HG(X)PRT) has been suggested as a target for development of new anti-malarial therapeutics. Acyclic nucleoside phosphonates (ANPs) are potent and selective inhibitors of plasmodial HG(X)PRTs. A new series of ANPs, based on the chemical structure and inhibitory activity of three ANPs, 2-(phosphonoethoxy)ethyl with either guanine or hypoxanthine as the base (PEEG and PEEHx) and 3-hydroxy-2-(phosphonomethoxy)propyl with guanine as the base (HPMPG), were prepared. These compounds are stereoisomers of 3-fluoro-(2-phosphonoethoxy)propyl (FPEPs) and 3-fluoro-(2-phosphonomethoxy)propyl (FPMPs) analogues. Both the (R)- and (S)-isomers of these fluorinated derivatives have higher K-i values (by 10- to 1000-fold) for human HGPRT and Plasmodium falciparum HGXPRT than the non-fluorinated ANPs. Possible explanations for these changes in affinity are proposed based on docking studies using the known crystal structures of human HGPRT in complex with PEEG. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.032
• 作为产物：
  描述：

  三苯甲基-(S)-缩水甘油醚 在 二氟化氢钾 、 tetrabutylammonium bifluoride 作用下， 以 氯苯 为溶剂， 反应 15.0h， 以82%的产率得到(+)-(2R)-1-fluoro-3-(triphenylmethoxy)propan-2-ol
  参考文献：
  名称：

  扩大3-氟-2-（膦酰基甲氧基）丙基无环核苷膦酸酯的抗病毒谱：天门冬氨酸二酰胺A酸酯前药

  摘要：

  已知含有3-氟-2-（膦酰基甲氧基）丙基（FPMP）侧链的无环核苷是中等效力的抗人免疫缺陷病毒（HIV）剂，而完全没有针对多种DNA病毒的抗病毒活性。FPMPs的膦酸官能团与天冬氨酸二戊基苯氧酰胺酯基团的衍生化产生了新一代的化合物，这些化合物不仅显示出极大的抗逆转录病毒效力，而且其活性范围广，还涵盖了乙型肝炎和疱疹病毒。最好的化合物，（S-FPMPA酰胺化物前药在低纳摩尔浓度下在TZM-b1和外周血单核细胞中发挥抗HIV-1活性，对乙型肝炎病毒（HBV）和水痘带状疱疹病毒（VZV）表现出出色的效力。该前药在酸性和人血浆介质中稳定，但在人肝微粒体中有效处理，半衰期为2分钟。（R）异构体鸟嘌呤衍生物作为选择性活性的抗HIV和抗HBV抑制剂出现，同时对人肝母细胞瘤细胞无毒。值得注意的是，含嘧啶的前药（S）-Asp-FPMPC是该系列中唯一显示微摩尔抗人巨细胞病毒（HCMV）效力的同类物。

  DOI：

  10.1021/acs.jmedchem.7b00416

文献信息

• Regioselective conversion of O-protected glycidols to fluorohydrins catalyuzed by tetrabutylammonium dihydrogentrifluoride under solid-liquid PTC conditions
  作者：Dario Landini、Domenico Albanese、Michele Penso

  DOI：10.1016/s0040-4020(01)92194-5

  日期：1992.1

  converted into the corresponding fluorohydrins FCH2CH(OH)CH2OX by reaction with catalytic amounts of Bu4N+H2F3- and a molar excess of KHF2. Most of the protective groups (X) examined are stable under the above conditions, moreover stereogenic carbons are not affected.

  许多ø -保护的缩水甘油被区域选择性地转化成相应的fluorohydrins FCH 2 CH（OH）CH 2用的卜催化量的反应OX 4 Ñ + ħ 2 ˚F 3 -和摩尔过量的KHF 2。所检查的大多数保护基（X）在上述条件下都是稳定的，而且立体碳不受影响。
• Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines
  作者：Ondřej Baszczyňski、Petr Jansa、Martin Dračínský、Blanka Klepetářová、Antonín Holý、Ivan Votruba、Erik de Clercq、Jan Balzarini、Zlatko Janeba

  DOI：10.1016/j.bmc.2011.02.050

  日期：2011.4

  An efficient method for the synthesis of N-9-[3-fluoro-2-(phosphonomethoxy) propyl] (FPMP) derivatives of purine bases has been developed. Both (R)- and (S)-enantiomers of the N-6-substituted FPMP derivatives of adenine and 2,6-diaminopurine were prepared and their anti-human immunodeficiency virus (HIV) and anti-Moloney murine sarcoma virus (MSV) activity was evaluated. Whereas none of the 6-substituted FPMPA derivatives showed any antiviral activity, several FPMPDAP derivatives had a moderate antiretroviral activity. Moreover, the data obtained from the study of the substrate activity of the active derivatives towards N-6-methyl-AMP aminohydrolase support the notion that the studied N-6-substituted FPMPDAP derivatives act as prodrugs of the antiretroviral FPMPG analogues. (C) 2011 Elsevier Ltd. All rights reserved.