(1R,2R)-1-<(4S,5R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-2,3-bis(1,1,2,2-tetramethyl-1-silapropoxy)propan-1-ol | 165674-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-1-<(4S,5R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-2,3-bis(1,1,2,2-tetramethyl-1-silapropoxy)propan-1-ol
• 英文别名: (1R,2R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[(4R,5S)-2,2-dimethyl-5-[(Z)-phenylmethoxyiminomethyl]-1,3-dioxolan-4-yl]propan-1-ol
• CAS: 165674-14-6
• 化学式: C₂₈H₅₁NO₆Si₂
• 分子量: 553.887
• InChiKey: NCAXLEWTHIAUEZ-VFSXNEHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-<(4S,5R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-2,3-bis(1,1,2,2-tetramethyl-1-silapropoxy)propan-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 正丁基锂 、 N-甲基吲哚酮 、 samarium diiodide 、 四丙基高钌酸铵 、 偶氮二异丁腈 、 Dowex H⁺ resin 、 氢氟酸 、 四丁基氟化铵 、 三正丁基氢锡 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 (+)-7-脱氧水鬼蕉碱
  参考文献：
  名称：

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

  摘要：

  DOI：

  10.1021/ja00132a047
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 吡啶 、 咪唑 、 二异丁基氢化铝 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 79.5h， 生成 (1R,2R)-1-<(4S,5R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-2,3-bis(1,1,2,2-tetramethyl-1-silapropoxy)propan-1-ol
  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

文献信息

• Diastereoselective 6-<i>e</i><i>xo</i> Radical Cyclizations of Oxime Ethers:  Total Synthesis of 7-Deoxypancratistatin
  作者：Gary E. Keck、Stanton F. McHardy、Jerry A. Murry

  DOI：10.1021/jo9902042

  日期：1999.6.1

  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.
• Total Synthesis of (+)-7-Deoxypancratistatin: A Radical Cyclization Approach
  作者：Gary E. Keck、Stanton F. McHardy、Jerry A. Murry

  DOI：10.1021/ja00132a047

  日期：1995.7