2-[(3aR,4S,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-hexahydro-furo[3,4-b]furan-6-yloxy]-isoindole-1,3-dione | 471241-75-5

• 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,4S,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-hexahydro-furo[3,4-b]furan-6-yloxy]-isoindole-1,3-dione
• 英文别名: 2-[[(3aR,4S,6aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-3a,4,6,6a-tetrahydro-3H-furo[2,3-c]furan-6-yl]oxy]isoindole-1,3-dione
• CAS: 471241-75-5
• 化学式: C₃₁H₃₁NO₇Si
• 分子量: 557.675
• InChiKey: JELMVHTZQMGELL-JUFCRRNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  91.4
• 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,4S,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-hexahydro-furo[3,4-b]furan-6-yloxy]-isoindole-1,3-dione 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 Formic acid (S)-1-((2S,3S)-2-allyl-5-oxo-tetrahydro-furan-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 、 Formic acid (S)-1-((2R,3S)-2-allyl-5-oxo-tetrahydro-furan-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester
  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：

  叔丁基二苯基氯硅烷 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 76.5h， 生成 2-[(3aR,4S,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-hexahydro-furo[3,4-b]furan-6-yloxy]-isoindole-1,3-dione
  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