methyl 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-gluco-non-8-eno-pyranoside | 182413-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-gluco-non-8-eno-pyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-[(1S)-1-phenylmethoxybut-3-enyl]oxane
• CAS: 182413-57-6
• 化学式: C₃₈H₄₂O₆
• 分子量: 594.748
• InChiKey: YMRFCCPAYOILOA-UYVXOPRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-gluco-non-8-eno-pyranoside 在 iodonium(di-γ-collidine) perchlorate 、 锌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal
  参考文献：
  名称：

  Allylated Monosaccharides as Precursors in Triple Reductive Amination Strategies:  Synthesis of Castanospermine and Swainsonine

  摘要：

  The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.

  DOI：

  10.1021/jo001447t
• 作为产物：
  描述：

  methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 tin 、 四丁基碘化铵 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 methyl 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-gluco-non-8-eno-pyranoside
  参考文献：
  名称：

  Triple Reductive Amination Approach to Polyhydroxyindolizidine Alkaloids:  A Total Synthesis of Castanospermine

  摘要：

  DOI：

  10.1021/jo961208z

文献信息

• Triple Reductive Amination Approach to Polyhydroxyindolizidine Alkaloids:  A Total Synthesis of Castanospermine
  作者：Hang Zhao、David R. Mootoo

  DOI：10.1021/jo961208z

  日期：1996.1.1
• Allylated Monosaccharides as Precursors in Triple Reductive Amination Strategies:  Synthesis of Castanospermine and Swainsonine
  作者：Hang Zhao、Sunej Hans、Xuhong Cheng、David R. Mootoo

  DOI：10.1021/jo001447t

  日期：2001.3.1

  The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.