(4S,5S)-5-[(R)-((S)-5,8-Dioxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-7-yl)-methoxymethoxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime | 165674-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (4S,5S)-5-[(R)-((S)-5,8-Dioxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-7-yl)-methoxymethoxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime
• CAS: 165674-19-1
• 化学式: C₂₆H₂₇NO₁₀
• 分子量: 513.501
• InChiKey: QWJCFQXWZGYTHU-PSSHSIDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  120.34
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-[(R)-((S)-5,8-Dioxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-7-yl)-methoxymethoxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 5.5h， 生成 (12aS,4R,12R,11bR,3aR,4aR)-4-(methoxymethoxy)-2,2-dimethyl-12-<(phenylmethoxy)amino>-4,12,11b,12a,3a,4a-hexahydro-9H-1,3-dioxoleno<4",5"-7',6'>isochromano<4',3'-5,4>benzo<4,5-d>-1,3-dioxolan-6-one
  参考文献：
  名称：

  Diastereoselective 6-exo Radical Cyclizations of Oxime Ethers:  Total Synthesis of 7-Deoxypancratistatin

  摘要：

  The development of an approach leading to the total synthesis of 7-deoxypancratistatin is described. The key features of the approach include a 6-exo radical cyclization reaction between a benzylic radical and an O-benzyloxime ether to establish the C-4a-C-10b bond. The stereochemistry of this reaction was examined in both acyclic radical precursors and ones in which the aryl moiety was tethered to the C-1 oxygen substituent. It was found that the use of such a tether was essential to obtain the stereochemical result required for the synthesis. The correct absolute and relative configurations at the hydroxylated carbons C-1-C-4 were obtained using D-gulonolactone as the source of C-10b-C-4a.

  DOI：

  10.1021/jo9902042
• 作为产物：
  描述：

  6-((2S,3R)-3-<(5S,4R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-(methoxymethoxy)-2-(1,1,2,2-tetramethyl-1-silapropoxy)propanoyl)-2H-benzo-1,3-dioxolane-5-carbaldehyde 在 吡啶 、 氢氟酸 、 戴斯-马丁氧化剂 作用下， 生成 (4S,5S)-5-[(R)-((S)-5,8-Dioxo-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromen-7-yl)-methoxymethoxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime
  参考文献：
  名称：

  Total Synthesis of (+)-7-Deoxypancratistatin: A Radical Cyclization Approach

  摘要：

  DOI：

  10.1021/ja00132a047