Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester | 250588-64-8

• 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: Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
• 英文别名: [(3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 250588-64-8
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: SMOJMZJHRRYKCM-FAXLKDOZSA-N

物化性质

• 沸点：
  504.3±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 在 吡啶 、 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 氨 、 caesium carbonate 、 六甲基二硅氮烷 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 28.0h， 生成 <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>
  参考文献：
  名称：

  TSAO类似物。1- [2'，5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-呋喃呋喃糖基] -3'-螺-5'-（4''-）的立体特异性合成和抗HIV-1活性氨基-1''，2''-草硫醇2''，2''-二氧化物）嘧啶和嘧啶修饰的核苷。

  摘要：

  抗HIV-1药物[1- [2'，5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-呋喃呋喃糖基]-胸腺嘧啶]的新铅的几种类似物-3'-spiro-5'在胸腺嘧啶部分的N-3，O-4和C-5位修饰的'-（4''-氨基-1''，2''-草硫醇2''，2''-二氧化物）（TSAO），已经制备并评估为HIV-1复制的抑制剂。描述了一种新的立体选择性合成方法。1,2-二-O-乙酰基-5-O-苯甲酰基-3-C-氰基-3-O-甲磺酰基-D-呋喃呋喃糖与嘧啶碱的反应，然后用Cs2CO3处理，得到立体选择性的β-D-呋喃呋喃糖基-3'-螺核苷。2′，5′-O-脱酰并随后用叔丁基二甲基甲硅烷基氯处理得到TSAO衍生物。仅那些在C-5'和C-2'均具有tBDMSi基团的类似物 核糖部分的位置显示出有效的抗HIV-1活性。活性范围为0.060μM至1.0μM。在胸腺嘧啶环的N-3处引入烷基或烯基官能团可显着降低细胞

  DOI：

  10.1021/jm00094a009
• 作为产物：
  描述：

  sodium cyanide 、 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 在 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 以87%的产率得到Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
  参考文献：
  名称：

  Preparation of Spiro[4.4]oxaphospholene and -azaphospholene Systems from Carbohydrate Templates

  摘要：

  Introduction of a spiro-phosphorus cycle in position 3 of monosaccharidic derivatives was studied starting from cyanohydrin or aminonitrile A. A two-step procedure involving (i) phosphonylation and (ii) carbanion-mediated phosphonate intramolecular cyclization (denoted CPIC) was used. The necessity of having an electron-withdrawing group alpha to the phosphorus atom in order to avoid undesired reactions was demonstrated.

  DOI：

  10.1021/jo400954p

文献信息

• Synthesis of phosphorus analogs of TSAO-T
  作者：Marina Moura、Solen Josse、Denis Postel

  DOI：10.1016/j.tet.2018.07.026

  日期：2018.9

  Phosphorus Analogs of TSAO bearing an oxaphospholene ring instead of an oxathiole dioxide ring at C-3′ position were prepared. Strategy developed previously on saccharidic moiety was used with introduction of an electron withdrawing α group neighboring the phosphorus atom. Biological evaluation on both HIV-1 and HCV showed that these compounds have no activity.

  制备了在C-3'位置带有氧杂磷烯环而不是二氧硫杂草酮环的TSAO的磷类似物。先前在糖基上开发的策略用于引入与磷原子相邻的吸电子α基团。对HIV-1和HCV的生物学评估表明，这些化合物没有活性。
• Synthesis, anti-HIV-1 activity, and modeling studies of N-3 Boc TSAO compound
  作者：Cyrille Tomassi、Albert Nguyen Van Nhien、José Marco-Contelles、Jan Balzarini、Christophe Pannecouque、Erik De Clercq、Elena Soriano、Denis Postel

  DOI：10.1016/j.bmcl.2008.03.010

  日期：2008.4

  The synthesis and the biological evaluation of the anti-HIV-1 activity of TSAO-Boc(3)T (8) are described. The computational analysis showed that the N-3 Boc group promotes new interactions in the binding site of the enzyme leading to a good inhibitory activity.

  描述了TSAO-Boc（3）T（8）的抗HIV-1活性的合成和生物学评估。计算分析表明，N-3 Boc基团在酶的结合位点促进了新的相互作用，从而导致了良好的抑制活性。
• Synthesis, NMR studies and theoretical calculations of novel 3-spiro-branched ribofuranoses
  作者：María-José Camarasa、María-Luisa Jimeno、María-Jesús Pérez-Pérez、Rosa Alvarez、Sonsoles Velázquez、Angel Lozano

  DOI：10.1016/s0040-4020(99)00696-1

  日期：1999.10

  Novel spiro-branched sugar derivatives bearing a spiro-5'-(4'-amino-2'-oxazolone) or a spiro-5'-(4'amino-1',2',3'-oxathiazole-2',2'-dioxide) rings at position-3 of the sugar moiety have been prepared. The synthesis has been achieved by a one-pot procedure from a conveniently protected sugar cyanohydrin derivative by reaction with chlorosulfonyl isocyanate or sulfamoyl chloride, respectively. The tautomeric preference in solution of these novel 3-spiro sugars are described as derived from NMR spectroscopy. Also a comparative theoretical study, by ab-initio methods, of the steric and electronic properties of the spiro rings present in these sugar derivatives has been performed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Steric and Electronic Properties of the 3′-spiro Moiety of TSAO-T and Analogues
  作者：M. J. Pérez-Pérez、R. Alvarez、M. L. Jimeno、A. San-Félix、A. Lozano、M. J. Camarasa

  DOI：10.1080/15257779908041661

  日期：1999.4

  The synthesis and study of geometrical and stereoelectronic properties of the spiro moiety of tof novel TSAO analogues modified at the 3'-spiro moiety is described.