(3S,4R,5S,6R,7R)-1,3,4,6,8-pentahydroxy-5,7-bis(phenylmethoxy)octan-2-one | 1004998-43-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5S,6R,7R)-1,3,4,6,8-pentahydroxy-5,7-bis(phenylmethoxy)octan-2-one
• CAS: 1004998-43-9
• 化学式: C₂₂H₂₈O₈
• 分子量: 420.46
• InChiKey: UVINPPATTUNQEJ-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6R,7R)-1,3,4,6,8-pentahydroxy-5,7-bis(phenylmethoxy)octan-2-one 、 乙酸酐 在 sodium acetate 作用下， 反应 2.0h， 以65%的产率得到Bn(-5)[Bn(-7)]D-gro-a-D-manOct2ulo1Ac2Ac3Ac4Ac8Ac
  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：

  (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 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (3S,4R,5S,6R,7R)-1,3,4,6,8-pentahydroxy-5,7-bis(phenylmethoxy)octan-2-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

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.