(2R)-2-[(4R,5R)-2,2-dimethyl-5-phenylmethoxy-1,3-dioxan-4-yl]-2-phenylmethoxyacetaldehyde | 1004998-42-8

• 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)-2-[(4R,5R)-2,2-dimethyl-5-phenylmethoxy-1,3-dioxan-4-yl]-2-phenylmethoxyacetaldehyde
• CAS: 1004998-42-8
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: AQPNVEVYVVDDGG-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(4R,5R)-2,2-dimethyl-5-phenylmethoxy-1,3-dioxan-4-yl]-2-phenylmethoxyacetaldehyde 、 2-tert-butyl-2-methyl-1,3-dioxan-5-one 在 L-脯氨酸 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以69%的产率得到(2R,4S)-4-((1S,2S)-2-(benzyloxy)-2-((4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl)-1-hydroxyethyl)-2-(tert-butyl)-2-methyl-1,3-dioxan-5-one
  参考文献：
  名称：

  Building carbohydrates on the dioxanone scaffold: stereoselective synthesis of d-glycero-d-manno-2-octulose

  摘要：

  The title compound has been synthesized via two proline-catalyzed aldol addition reactions of 2,2-dialkyl-1,3-dioxan-5ones: the first addition to 1,3-dithiane-2-carboxaldehyde, followed by reduction to the corresponding diol, protection of the OH groups and dithiane hydrolysis afforded a protected D-ribose that was used in the second aldol addition reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.100
• 作为产物：
  描述：

  (4R,5R)-4-[(R)-1,3-dithian-2-yl(phenylmethoxy)methyl]-2,2-dimethyl-5-phenylmethoxy-1,3-dioxane 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以69%的产率得到(2R)-2-[(4R,5R)-2,2-dimethyl-5-phenylmethoxy-1,3-dioxan-4-yl]-2-phenylmethoxyacetaldehyde
  参考文献：
  名称：

  Building carbohydrates on the dioxanone scaffold: stereoselective synthesis of d-glycero-d-manno-2-octulose

  摘要：

  The title compound has been synthesized via two proline-catalyzed aldol addition reactions of 2,2-dialkyl-1,3-dioxan-5ones: the first addition to 1,3-dithiane-2-carboxaldehyde, followed by reduction to the corresponding diol, protection of the OH groups and dithiane hydrolysis afforded a protected D-ribose that was used in the second aldol addition reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.100

文献信息

• Building carbohydrates on the dioxanone scaffold: stereoselective synthesis of d-glycero-d-manno-2-octulose
  作者：Nagarjuna Palyam、Izabella Niewczas、Marek Majewski

  DOI：10.1016/j.tetlet.2007.10.100

  日期：2007.12

  The title compound has been synthesized via two proline-catalyzed aldol addition reactions of 2,2-dialkyl-1,3-dioxan-5ones: the first addition to 1,3-dithiane-2-carboxaldehyde, followed by reduction to the corresponding diol, protection of the OH groups and dithiane hydrolysis afforded a protected D-ribose that was used in the second aldol addition reaction. (c) 2007 Elsevier Ltd. All rights reserved.