(5S)-3,6-dideoxy-1,2-O-isopropylidene-5-hydroxy-6-(methyl hex-1-ynoate)-α-D-ribo-hexofuranose | 939378-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5S)-3,6-dideoxy-1,2-O-isopropylidene-5-hydroxy-6-(methyl hex-1-ynoate)-α-D-ribo-hexofuranose
• 英文别名: methyl (8S)-8-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-8-hydroxyoct-5-ynoate
• CAS: 939378-85-5
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: JICJYVNRFXQESJ-RMRHIDDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5S)-3,6-dideoxy-1,2-O-isopropylidene-5-hydroxy-6-(methyl hex-1-ynoate)-α-D-ribo-hexofuranose 在 nickel diacetate 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 silica gel 、 乙二胺 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， -90.0~50.0 ℃ 、101.33 kPa 条件下， 反应 73.5h， 生成 (S,Z)-1-((2S,4S,5S)-4-(benzoyloxy)-5-((Z)-oct-2-en-1-yl)tetrahydrofuran-2-yl)-8-methoxy-8-oxooct-3-en-1-yl benzoate
  参考文献：
  名称：

  Epoxygenase eicosanoids: Synthesis of tetrahydrofuran-diol metabolites and their vasoactivity

  摘要：

  Eight members of a recently identified family of tetrahydrofuran-diols (THFDs), originating from epoxyeicosatrienoic acids (EETs), were prepared stereospecifically from D-(+)-glucose. The THFDs potently induced relaxation of pre-contracted bovine arteries. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.096
• 作为产物：
  描述：

  5,6-脱水-3-脱氧-1,2-O-(1-甲基亚乙基)-beta-L-呋喃来苏己糖 在 甲醇 、 六甲基磷酰三胺 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 (5S)-3,6-dideoxy-1,2-O-isopropylidene-5-hydroxy-6-(methyl hex-1-ynoate)-α-D-ribo-hexofuranose
  参考文献：
  名称：

  Epoxygenase eicosanoids: Synthesis of tetrahydrofuran-diol metabolites and their vasoactivity

  摘要：

  Eight members of a recently identified family of tetrahydrofuran-diols (THFDs), originating from epoxyeicosatrienoic acids (EETs), were prepared stereospecifically from D-(+)-glucose. The THFDs potently induced relaxation of pre-contracted bovine arteries. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.096

文献信息

• Total Synthesis of (15<i>R</i>)- and (15<i>S</i>)-F_2t-Isoprostanes by a Biomimetic Process Using the Cyclization of Acyclic Dihydroxylated Octa-5,7-dienyl Radicals
  作者：Thierry Durand、Alexandre Guy、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1021/jo0109624

  日期：2002.5.1

  We report a new route to F-2t-IsoP (formerly named 8-epi-PGF(2alpha)) using a biomimetic radical cyclization of a highly functionalized C20 precursor. The strategy employed gives a beta-hydroxy free radical followed by molecular oxygen trapping, which is an unusual method for quenching carbon free radicals. We observed the formation of unique diastereoisomers (15R)- and (15S)-F-2t-IsoP. This result is consistent with a strong stereoelectronic control associated with a steric effect initiated by the side chains alpha and omega on the cyclopentane ring.