5-deoxy-1,2-O-isopropylidene-3-O-(p-methoxyphenyl)methyl-5-C-(n-nonyl)-α-D-xylofuranose | 224297-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-deoxy-1,2-O-isopropylidene-3-O-(p-methoxyphenyl)methyl-5-C-(n-nonyl)-α-D-xylofuranose
• 英文别名: (3aR,5R,6S,6aR)-5-decyl-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 224297-53-4
• 化学式: C₂₅H₄₀O₅
• 分子量: 420.59
• InChiKey: STPWGLCJIBXWED-UEQSERJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 5-deoxy-1,2-O-isopropylidene-3-O-(p-methoxyphenyl)methyl-5-C-(n-nonyl)-α-D-xylofuranose 在 Amberlite IR 120 H⁺ 作用下， 反应 6.0h， 以34%的产率得到methyl 5-deoxy-3-O-(p-methoxyphenyl)methyl-5-C-(n-nonyl)-β-D-xylofuranoside
  参考文献：
  名称：

  Radical cyclisation approach for the first synthesis and determination of absolute stereochemistry of discosiolide from diacetone glucose

  摘要：

  By the adoption of a regio- and stereoselective intramolecular radical cyclisation reaction onto a chiron derived from diacetone glucose, the crucial cis-fused bicyclo[3.3.0]octane system was made and utilized for the first synthesis of discosiolide 1, thereby establishing the absolute stereochemistry of the natural product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00057-9
• 作为产物：
  描述：

  (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 乙醇 为溶剂， 反应 13.5h， 生成 5-deoxy-1,2-O-isopropylidene-3-O-(p-methoxyphenyl)methyl-5-C-(n-nonyl)-α-D-xylofuranose
  参考文献：
  名称：

  Radical cyclisation approach for the first synthesis and determination of absolute stereochemistry of discosiolide from diacetone glucose

  摘要：

  By the adoption of a regio- and stereoselective intramolecular radical cyclisation reaction onto a chiron derived from diacetone glucose, the crucial cis-fused bicyclo[3.3.0]octane system was made and utilized for the first synthesis of discosiolide 1, thereby establishing the absolute stereochemistry of the natural product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00057-9

文献信息

• Radical cyclisation approach for the first synthesis and determination of absolute stereochemistry of discosiolide from diacetone glucose
  作者：G.V.M Sharma、Kasireddy Krishnudu

  DOI：10.1016/s0957-4166(99)00057-9

  日期：1999.3

  By the adoption of a regio- and stereoselective intramolecular radical cyclisation reaction onto a chiron derived from diacetone glucose, the crucial cis-fused bicyclo[3.3.0]octane system was made and utilized for the first synthesis of discosiolide 1, thereby establishing the absolute stereochemistry of the natural product. (C) 1999 Elsevier Science Ltd. All rights reserved.