(4R,5R)-4-[(R)-1,3-dithian-2-yl(hydroxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ol | 1004998-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-[(R)-1,3-dithian-2-yl(hydroxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ol
• CAS: 1004998-39-3
• 化学式: C₁₁H₂₀O₄S₂
• 分子量: 280.409
• InChiKey: ITARUHJRYJEOSS-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-[(R)-1,3-dithian-2-yl(hydroxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ol 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以87%的产率得到(4R,5R)-4-[(R)-1,3-dithian-2-yl(phenylmethoxy)methyl]-2,2-dimethyl-5-phenylmethoxy-1,3-dioxane
  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：

  (S)-4-((R)-[1,3]Dithian-2-yl-hydroxy-methyl)-2,2-dimethyl-[1,3]dioxan-5-one 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 (4R,5R)-4-[(R)-1,3-dithian-2-yl(hydroxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ol
  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.