(2R,3R)-3-Benzyloxy-3-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-propane-1,2-diol | 688317-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-3-Benzyloxy-3-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-propane-1,2-diol
• 英文别名: (2R,3R)-3-[(4S,5S)-5-ethenyl-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-3-phenylmethoxypropane-1,2-diol
• CAS: 688317-58-0
• 化学式: C₂₅H₃₂O₆
• 分子量: 428.525
• InChiKey: SSWYHZQSQJKSFX-AHCIIZGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (2R,3R)-3-Benzyloxy-3-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-propane-1,2-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 四氧化锇 、 N-甲基吗啉氧化物 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 水 、 丙酮 、 丁酮 、 苯 为溶剂， 反应 28.0h， 生成 (3aR,4R,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,5-diol
  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：

  2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 硫酸 、 sodium hydride 、 sodium amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (2R,3R)-3-Benzyloxy-3-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-propane-1,2-diol
  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.