(2S,3S,4R,5R,6R)-3-(Mesyloxy)-6-Methoxy-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-2,3,4,5-tetrahydro-4,5-dimethyl-6H-pyran-4,5-diol | 150254-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-3-(Mesyloxy)-6-Methoxy-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-2,3,4,5-tetrahydro-4,5-dimethyl-6H-pyran-4,5-diol
• CAS: 150254-37-8
• 化学式: C₁₄H₂₆O₉S
• 分子量: 370.421
• InChiKey: KXFVUSGNLOJGPK-FZGPNCDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120.75
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-3-(Mesyloxy)-6-Methoxy-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-2,3,4,5-tetrahydro-4,5-dimethyl-6H-pyran-4,5-diol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以99%的产率得到(2S,3R,4R,5R,6R)-6-Methoxy-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-2,3,4,5-tetrahydro-4,5-dimethyl-3,4-epoxy-6H-pyran-5-ol
  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：

  (2S,3S)-3-<2-(3,4-Dimethylfuryl)>-1,2-O-isopropylideneglycerol 在 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 cerium(III) chloride 、 sodium acetate 、 sodium hydrogensulfite 、 三乙胺 、 silver(I) iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 31.0h， 生成 (2S,3S,4R,5R,6R)-3-(Mesyloxy)-6-Methoxy-2-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-2,3,4,5-tetrahydro-4,5-dimethyl-6H-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