2-[(3aR,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-isoindole-1,3-dione | 251460-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[(3aR,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-isoindole-1,3-dione
• 英文别名: 2-[[(3aR,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxy]isoindole-1,3-dione
• CAS: 251460-68-1
• 化学式: C₂₂H₃₁NO₇Si
• 分子量: 449.576
• InChiKey: WQKXNPSYHBNFEA-GXIXOUGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  烯丙基三丁基锡 、 2-[(3aR,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-isoindole-1,3-dione 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 3.5h， 以65%的产率得到1,2,3-trideoxy-4,5-O-isopropylidne-D-arabino-hept-1-enitol
  参考文献：
  名称：

  Sequential alkoxy radical fragmentation–intermolecular allylation in carbohydrate systems

  摘要：

  The C-radical originated by beta-fragmentation of carbohydrate anomeric alkoxy radicals, generated under reductive conditions by treatment of N-phthalimido glycosides with allyltri-n-butyltin/AIBN may subsequently undergo ail intermolecular allylation to give hept-1-enitol derivatives. These compounds can be useful chiral synthons for the synthesis of polyhydroxylated compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00911-5
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到2-[(3aR,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-isoindole-1,3-dione
  参考文献：
  名称：

  通过N-邻苯二甲酰亚胺基糖苷的还原性自由基断裂合成醛糖醇。手性合成中间体的制备

  摘要：

  的反应Ñ -phthalimido glycofuranosides并用glycopyranosides通过异头烷氧基自由基的形成产生碳水化合物C1C2键的自由基β-碎片。这构成了一种新的两步法，可轻松地将碳水化合物转化为碳含量低的相应无环醛糖醇。

  DOI：

  10.1016/s0040-4039(99)01482-3

文献信息

• Reductive Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. Synthesis of Alditols with Potential Utility as Chiral Synthons
  作者：Cosme G. Francisco、Elisa I. León、Angeles Martín、Pilar Moreno、María S. Rodríguez、Ernesto Suárez

  DOI：10.1021/jo0156565

  日期：2001.10.1

  A series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1-C2 fragmentation reaction under reductive conditions. This reaction constitutes a two-step method for the transformation of carbohydrates into the corresponding alditols with one less carbon. Using

  合成了一系列呋喃糖和吡喃糖形式的碳水化合物的异头硝酸酯和N-邻苯二甲酰亚胺基糖苷，以生成相应的烷氧基，并研究还原条件下的C1-C2片段化反应。该反应构成了将碳水化合物转化为碳较少的相应糖醇的两步法。使用这种方法，已经制备了具有D-赤藓糖醇，D-苏糖醇，D-木糖醇和D-阿拉伯糖醇立体化学的天然产物合成的有趣的四碳和五碳构件。1,2-O-异亚丙基-β-L-苏糖（40）和1-乙酰氨基-2,4,5-三-O-乙酰基-D-阿拉伯糖醇（50）的合成也已从1,2实现：5,6-二-O-异亚丙基-β-D-呋喃葡萄糖和2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-D-吡喃葡萄糖，
• Synthesis of alditols by reductive radical fragmentation of N-phthalimido glycosides. Preparation of chiral synthetic intermediates
  作者：Angeles Martín、María S. Rodríguez、Ernesto Suárez

  DOI：10.1016/s0040-4039(99)01482-3

  日期：1999.10

  The reaction of N-phthalimido glycofuranosides and glycopyranosides with produces radical β-fragmentation of the carbohydrate C1C2 bond through the formation of anomeric alkoxy radicals. This constitutes a new two-step methodology for the facile conversion of carbohydrates into the corresponding acyclic alditols with one fewer carbon.

  的反应Ñ -phthalimido glycofuranosides并用glycopyranosides通过异头烷氧基自由基的形成产生碳水化合物C1C2键的自由基β-碎片。这构成了一种新的两步法，可轻松地将碳水化合物转化为碳含量低的相应无环醛糖醇。
• Sequential alkoxy radical fragmentation–intermolecular allylation in carbohydrate systems
  作者：Angeles Martı́n、Inés Pérez-Martı́n、Ernesto Suárez

  DOI：10.1016/s0040-4039(02)00911-5

  日期：2002.7

  The C-radical originated by beta-fragmentation of carbohydrate anomeric alkoxy radicals, generated under reductive conditions by treatment of N-phthalimido glycosides with allyltri-n-butyltin/AIBN may subsequently undergo ail intermolecular allylation to give hept-1-enitol derivatives. These compounds can be useful chiral synthons for the synthesis of polyhydroxylated compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.