1,5-anhydro-2-deoxy-6-O-pivaloyl-D-lyxo-hex-1-enitol | 185803-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,5-anhydro-2-deoxy-6-O-pivaloyl-D-lyxo-hex-1-enitol
• 英文别名: 6-O-pivaloyl-galactal；[(2R,3R,4R)-3,4-dihydroxy-3,4-dihydro-2H-pyran-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 185803-62-7
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: LTIHNSOBKIFNDG-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2-deoxy-6-O-pivaloyl-D-lyxo-hex-1-enitol 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 三丁基氧化锡 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 3.5h， 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
• 作为产物：
  描述：

  (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 、 3-pivaloylthiazolidine-2-thione 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到1,5-anhydro-2-deoxy-6-O-pivaloyl-D-lyxo-hex-1-enitol
  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

• Glycal Glycosylation and 2-Nitroglycal Concatenation, a Powerful Combination for Mucin Core Structure Synthesis
  作者：Jürgen Geiger、B. Gopal Reddy、Gottfried A. Winterfeld、R. Weber、M. Przybylski、R. R. Schmidt

  DOI：10.1021/jo061670b

  日期：2007.6.1

  3-O-glycosylated with O-(galactopyranosyl) trichloroacetimidates; depending on the protecting group pattern stereoselectively α- and β-linked disaccharides were obtained. With O-(2-azido-2-deoxyglucopyransyl) trichloroacetimidate as donor (compound 10A), glycosylation of 2 and of a 6-O-unprotected galactal derivative led in acetonitrile as solvent exclusively to a β(1−3)- and a β(1−6)-linked disaccharide, respectively

  具有大的6- O- TIPS保护作用的3，4- O-未保护的半乳糖衍生物（化合物2）可以被O-（吡喃半乳糖基）三氯乙酰亚氨酸盐区域选择性地3- O-糖基化。根据保护基的模式，立体选择性地获得α-和β-连接的二糖。以O-（2-叠氮基-2-脱氧葡萄糖吡喃基）三氯乙酰亚氨酸酯为供体（化合物10A），对2和6- O进行糖基化-未保护的半乳糖衍生物在乙腈中仅作为溶剂分别引至β（1-3）-和β（1-6）连接的二糖。糖的半乳糖部分硝化，然后通过迈克尔型添加丝氨酸和苏氨酸衍生物（7a，b）安装了α-半乳糖构型，因此很容易提供O-糖基氨基酸结构单元，用于将核1，核2，核3，核6和核8结构掺入糖肽中。2-硝基半乳糖和2-硝基葡糖衍生物也可以成功地通过迈克尔型加成以重复方式成功地用于糖苷键的形成，从而提供了相应的核心5，核心7和核心6构件。在这种方法中，高度立体选择性的糖苷键的形成仅基于2-型硝基糖的硝基-烯醇
• 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.