methyl 2,3,4,7-tetra-O-benzyl-D-glycero-α-D-galacto-heptopyranoside | 321142-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,7-tetra-O-benzyl-D-glycero-α-D-galacto-heptopyranoside
• 英文别名: (1R)-1-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-2-phenylmethoxyethanol
• CAS: 321142-25-0
• 化学式: C₃₆H₄₀O₇
• 分子量: 584.709
• InChiKey: GEKGXLHTUKOYKK-YCDIQEPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,7-tetra-O-benzyl-D-glycero-α-D-galacto-heptopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以89.3%的产率得到Methyl D-glycero-α-D-galacto-heptopyranoside
  参考文献：
  名称：

  格利雅C 1试剂保护己糖的同系物

  摘要：

  使三种立体异构体己二醛-1,5-吡喃糖苷的衍生物与四种格氏试剂C 1反应：甲氧基甲基氯化物，烯丙氧基甲基氯化物，苄氧基甲基氯化物和二甲基苯基甲硅烷基甲基氯化镁。在每种情况下均以良好的产率获得了两种立体异构的庚糖。甲基同种异体甙衍生的庚糖甙伴随有C-5倒置产物。成醛添加格氏试剂5 - 8在平行α-或β-螯合和Felkin-映过渡态的形式进行了讨论。已经发现，甲硅烷基格氏试剂12对于在C-6处形成l-构型的庚糖衍生物表现出强烈的偏好。

  DOI：

  10.1016/s0040-4020(00)00847-4
• 作为产物：
  描述：

  magnesium,methanidyloxymethylbenzene,chloride 、 methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside 在 (S)-(-)-1-甲基-2-(1-哌啶基甲基)吡咯烷 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 2,3,4,7-tetra-O-benzyl-D-glycero-α-D-galacto-heptopyranoside 、 methyl 2,3,4,7-tetra-O-benzyl-L-glycero-α-D-galacto-heptopyranoside
  参考文献：
  名称：

  Improving the stereoselectivity of one-carbon atom homologation of hexoses at the terminal position

  摘要：

  A number of modifications of the original Grignard C-1 homologation of hexoses as examined, e.g. reactions of protected hexodialdo-1,5-pyranosides with benzyloxymethyllithium, transmetalation, precomplexation of the aldehydes. Some of the modifications, e.g. benzyloxymethyl Grignard addition in the presence of tert amines showed good to very good stereoselectivity of the heptoside formation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02376-0

文献信息

• Homologation of Protected Hexoses with Grignard C1 Reagents
  作者：Mikhail Kim、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0040-4020(00)00847-4

  日期：2000.11

  hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5–8 has been discussed in terms

  使三种立体异构体己二醛-1,5-吡喃糖苷的衍生物与四种格氏试剂C 1反应：甲氧基甲基氯化物，烯丙氧基甲基氯化物，苄氧基甲基氯化物和二甲基苯基甲硅烷基甲基氯化镁。在每种情况下均以良好的产率获得了两种立体异构的庚糖。甲基同种异体甙衍生的庚糖甙伴随有C-5倒置产物。成醛添加格氏试剂5 - 8在平行α-或β-螯合和Felkin-映过渡态的形式进行了讨论。已经发现，甲硅烷基格氏试剂12对于在C-6处形成l-构型的庚糖衍生物表现出强烈的偏好。
• Improving the stereoselectivity of one-carbon atom homologation of hexoses at the terminal position
  作者：Mikhail Kim、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0040-4039(01)02376-0

  日期：2002.2

  A number of modifications of the original Grignard C-1 homologation of hexoses as examined, e.g. reactions of protected hexodialdo-1,5-pyranosides with benzyloxymethyllithium, transmetalation, precomplexation of the aldehydes. Some of the modifications, e.g. benzyloxymethyl Grignard addition in the presence of tert amines showed good to very good stereoselectivity of the heptoside formation. (C) 2002 Elsevier Science Ltd. All rights reserved.