(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methanol | 688317-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methanol
• 英文别名: (R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4S,5S)-5-ethenyl-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 688317-56-8
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: ITWYJSKMEIZDOX-PUHVVEEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methanol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 硫酸 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 、 苯 为溶剂， 反应 26.0h， 生成 (3aS,4R,6aS)-4-Benzyloxy-6a-benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole
  参考文献：
  名称：

  Synthesis of differentially protected cyclopentitol: its application towards the stereoselective synthesis of 5-epi-calditol

  摘要：

  The synthesis of differentially protected cyclopentitol derivative 5 is described using ring-closing metathesis of a diene derived froni D-mannose. Subsequent chemical 11 modifications such as catalytic osmylation and chain extension using glycidyl triflate completed the synthesis of 5-epi-calditol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.020
• 作为产物：
  描述：

  甲基三苯基碘化膦 、 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 sodium amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 以83%的产率得到(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methanol
  参考文献：
  名称：

  Synthesis of differentially protected cyclopentitol: its application towards the stereoselective synthesis of 5-epi-calditol

  摘要：

  The synthesis of differentially protected cyclopentitol derivative 5 is described using ring-closing metathesis of a diene derived froni D-mannose. Subsequent chemical 11 modifications such as catalytic osmylation and chain extension using glycidyl triflate completed the synthesis of 5-epi-calditol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.020

文献信息

• Synthesis of differentially protected cyclopentitol: its application towards the stereoselective synthesis of 5-epi-calditol
  作者：C.V. Ramana、Bethi Sridhar Reddy、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2004.02.020

  日期：2004.3

  The synthesis of differentially protected cyclopentitol derivative 5 is described using ring-closing metathesis of a diene derived froni D-mannose. Subsequent chemical 11 modifications such as catalytic osmylation and chain extension using glycidyl triflate completed the synthesis of 5-epi-calditol. (C) 2004 Elsevier Ltd. All rights reserved.