(2R,3S,4R,5R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-2H-pyran-4,5-diol | 150254-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-2H-pyran-4,5-diol
• 英文别名: (2S,3R,4R,5S,6R)-2-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4,5-trimethyloxane-3,4-diol
• CAS: 150254-46-9
• 化学式: C₁₉H₃₈O₆Si
• 分子量: 390.593
• InChiKey: CZXCUSJGVSVZCD-KHSMQWPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二甲醇缩甲醛 、 (2R,3S,4R,5R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-2H-pyran-4,5-diol 在 phosphorus pentoxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到(2R,3S,4R,5R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-1,3-dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-4,5-(methylenedioxy)-2H-pyran
  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：

  叔丁基二甲基氯硅烷 在 Wilkinson's catalyst 吡啶 、 四氧化锇 、 potassium tert-butylate 、 氢气 、 sodium hydrogensulfite 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， -30.0~70.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 (2R,3S,4R,5R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-2H-pyran-4,5-diol
  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.