(2S,6R)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-4,5-dimethyl-6H-pyran-3(2H)-one | 150336-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,6R)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-4,5-dimethyl-6H-pyran-3(2H)-one
• 英文别名: (2R,6S)-2-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dimethyl-2H-pyran-5-one
• CAS: 150336-61-1
• 化学式: C₁₈H₃₂O₅Si
• 分子量: 356.535
• InChiKey: SESBMYZSNWHTIU-CWRNSKLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,6R)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-4,5-dimethyl-6H-pyran-3(2H)-one 在 吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 四丁基氟化铵 、 sodium hydrogensulfite 、 silver(I) iodide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 30.5h， 生成 (2R,3S,4R,5R,6R)-6-Methoxy-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-3,4,5,6-tetrahydro-4,5-dimethyl-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthetic studies on macropyrrolizidine alkaloid, monocrotaline: enantioselective synthesis of a necic acid moiety, monocrotalic acid methylene acetal

  摘要：

  A methylene acetal derivative 4 of the necic acid, monocrotalic acid, part of the macropyrrolizidine alkaloid, monocrotaline, was enantioselectively synthesized from 2-furylmethanol derivative 6. Oxidation of 6, followed by silylation of the resulting lactol 9, gave silyl ether 19 as a major product. Introduction of the di-tert-hydroxy groups to 22 was achieved by stereoselective dihydroxylation with osmium tetroxide. After protection of the vicinal diol as a methylenedioxy derivative, acetal 26 was successfully converted into the desired product 4.

  DOI：

  10.1021/jo00068a022
• 作为产物：
  描述：

  Lithium 3,4-dimethylfuran-2-ide 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 silver(l) oxide 、 zinc dibromide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (2S,6R)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-4,5-dimethyl-6H-pyran-3(2H)-one
  参考文献：
  名称：

  Synthetic studies on macropyrrolizidine alkaloid, monocrotaline: enantioselective synthesis of a necic acid moiety, monocrotalic acid methylene acetal

  摘要：

  A methylene acetal derivative 4 of the necic acid, monocrotalic acid, part of the macropyrrolizidine alkaloid, monocrotaline, was enantioselectively synthesized from 2-furylmethanol derivative 6. Oxidation of 6, followed by silylation of the resulting lactol 9, gave silyl ether 19 as a major product. Introduction of the di-tert-hydroxy groups to 22 was achieved by stereoselective dihydroxylation with osmium tetroxide. After protection of the vicinal diol as a methylenedioxy derivative, acetal 26 was successfully converted into the desired product 4.

  DOI：

  10.1021/jo00068a022

文献信息

• Synthetic studies on macropyrrolizidine alkaloid, monocrotaline: enantioselective synthesis of a necic acid moiety, monocrotalic acid methylene acetal
  作者：Toshio Honda、Kunio Tomitsuka、Masayoshi Tsubuki

  DOI：10.1021/jo00068a022

  日期：1993.7

  A methylene acetal derivative 4 of the necic acid, monocrotalic acid, part of the macropyrrolizidine alkaloid, monocrotaline, was enantioselectively synthesized from 2-furylmethanol derivative 6. Oxidation of 6, followed by silylation of the resulting lactol 9, gave silyl ether 19 as a major product. Introduction of the di-tert-hydroxy groups to 22 was achieved by stereoselective dihydroxylation with osmium tetroxide. After protection of the vicinal diol as a methylenedioxy derivative, acetal 26 was successfully converted into the desired product 4.