(2S,3S)-3-<2-(3,4-Dimethylfuryl)>-1,2-O-isopropylideneglycerol | 150254-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-3-<2-(3,4-Dimethylfuryl)>-1,2-O-isopropylideneglycerol
• 英文别名: (S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(3,4-dimethylfuran-2-yl)methanol
• CAS: 150254-31-2
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: KKDFOCSOUOZPLY-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-<2-(3,4-Dimethylfuryl)>-1,2-O-isopropylideneglycerol 在 rhodium on alumina N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 氢气 、 sodium acetate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -30.0~70.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 (2R,3R,4S,5S,6S)-6-<(tert-Butyldimethylsilyl)oxy>-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-2,3,4,5-tetrahydro-3,4,5-trimethyl-6H-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：

  Lithium 3,4-dimethylfuran-2-ide 、 L-甘油醛缩丙酮 在 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (2S,3S)-3-<2-(3,4-Dimethylfuryl)>-1,2-O-isopropylideneglycerol 、 (2S,3R)-3-<2-(3,4-Dimethylfuryl)>-1,2-O-isopropylideneglycerol
  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.