1,4-anhydro-2-deoxy-6-O-pivaloyl-β-D-lyxo-hexopyranose | 185803-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-anhydro-2-deoxy-6-O-pivaloyl-β-D-lyxo-hexopyranose
• 英文别名: [(1S,3R,4R,5R)-5-hydroxy-2,7-dioxabicyclo[2.2.1]heptan-3-yl]methyl 2,2-dimethylpropanoate
• CAS: 185803-65-0
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: VODSYVVAZZUEAI-LURQLKTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-6-O-pivaloyl-β-D-lyxo-hexopyranose 在 吡啶 、 4-二甲氨基吡啶 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 methyl 3,5-di-O-acetyl-2-deoxy-6-O-pivaloyl-β-D-lyxo-hexofuranoside
  参考文献：
  名称：

  Stereocontrolled synthesis of O- and C-furanosides through 1,4-iodocyclisation of d-galactal

  摘要：

  Iodocyclisation of 6-O-protected-D-galactal, followed by radical reduction, gives [2.2.1] bicyclic acetals which are regioselectively opened by various nucleophiles (alcohols, allyltrimethylsilane, triphenylphosphine) to give furanosyl compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00480-9
• 作为产物：
  描述：

  3-pivaloylthiazolidine-2-thione 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 4.5h， 生成 1,4-anhydro-2-deoxy-6-O-pivaloyl-β-D-lyxo-hexopyranose
  参考文献：
  名称：

  Stereocontrolled synthesis of O- and C-furanosides through 1,4-iodocyclisation of d-galactal

  摘要：

  Iodocyclisation of 6-O-protected-D-galactal, followed by radical reduction, gives [2.2.1] bicyclic acetals which are regioselectively opened by various nucleophiles (alcohols, allyltrimethylsilane, triphenylphosphine) to give furanosyl compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00480-9

文献信息

• Synthesis of a tetrahydrofuran fragment of annonaceous acetogenin from d-galactal
  作者：Lénaïck Lemée、Anne Jégou、Alain Veyrières

  DOI：10.1016/s0040-4039(99)00322-6

  日期：1999.4

  Iodocyclisation of 6-O-pivaloyl-D-galactal followed by radical reduction at C-2 and S-N 2 conversion to a 3-endo iodide gave in good yield a [2.2.1] bicyclic acetal which can be regioselectively opened by C-nucleophiles (allyl silane or silyloxyfuran) in the presence of a Lewis acid to give 2,5-trans-disubstituted tetrahydrofurans. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereocontrolled synthesis of O- and C-furanosides through 1,4-iodocyclisation of d-galactal
  作者：Véronique Jaouen、Anne Jégou、Lénaïck Lemée、Alain Veyrières

  DOI：10.1016/s0040-4020(99)00480-9

  日期：1999.7

  Iodocyclisation of 6-O-protected-D-galactal, followed by radical reduction, gives [2.2.1] bicyclic acetals which are regioselectively opened by various nucleophiles (alcohols, allyltrimethylsilane, triphenylphosphine) to give furanosyl compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.