[(2R,3S,4R,5R,6R)-5-acetyloxy-1-formyl-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-prop-2-enylpiperidin-3-yl] acetate | 606970-32-5

• 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,3S,4R,5R,6R)-5-acetyloxy-1-formyl-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-prop-2-enylpiperidin-3-yl] acetate
• CAS: 606970-32-5
• 化学式: C₂₈H₃₃NO₇
• 分子量: 495.573
• InChiKey: DQVRCUWFTFELHO-RKFAPSRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丙烯酸乙酯 、 [(2R,3S,4R,5R,6R)-5-acetyloxy-1-formyl-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-prop-2-enylpiperidin-3-yl] acetate 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(E)-4-((2R,3S,4R,5R,6R)-3,5-Diacetoxy-4-benzyloxy-6-benzyloxymethyl-1-formyl-piperidin-2-yl)-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  General Access to Iminosugar C-Glycoside Building Blocks by Means of Cross-Metathesis:  A Gateway to Glycoconjugate Mimetics

  摘要：

  [GRAPHICS]Cross-metathesis reactions of alpha-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The reactions showed reasonable to very good yields and excellent E/Z selectivity. This methodology allows the efficient and convergent synthesis of iminosugar C-glycosides with a great degree of structural diversity in the aglycone, opening the way to a variety of new glycoconjugate mimetics of biological interest.

  DOI：

  10.1021/ol035117h
• 作为产物：
  描述：

  (2R,3S,4R,5R,6R)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-1-naphthalen-2-ylmethyl-piperidine-3,5-diol 在 吡啶 、 三甲基乙酰氯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 [(2R,3S,4R,5R,6R)-5-acetyloxy-1-formyl-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-prop-2-enylpiperidin-3-yl] acetate
  参考文献：
  名称：

  General Access to Iminosugar C-Glycoside Building Blocks by Means of Cross-Metathesis:  A Gateway to Glycoconjugate Mimetics

  摘要：

  [GRAPHICS]Cross-metathesis reactions of alpha-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The reactions showed reasonable to very good yields and excellent E/Z selectivity. This methodology allows the efficient and convergent synthesis of iminosugar C-glycosides with a great degree of structural diversity in the aglycone, opening the way to a variety of new glycoconjugate mimetics of biological interest.

  DOI：

  10.1021/ol035117h