methyl (2R,3S)-3-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-3-hydroxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]propanoate | 566198-52-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,3S)-3-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-3-hydroxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]propanoate
• CAS: 566198-52-5
• 化学式: C₂₈H₃₄N₂O₁₁
• 分子量: 574.585
• InChiKey: RQSQELWHHYNCMM-MYSWHGEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-3-hydroxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]propanoate 在 氢气 、 镍 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以75%的产率得到methyl (2R,3S)-3-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-amino-3-hydroxypropanoate
  参考文献：
  名称：

  Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins

  摘要：

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00460-x
• 作为产物：
  描述：

  2,3-邻异亚丙基-1-邻甲基-D-核糖酸 在 (S)-BinapRuBr₂ 、 氢气 、 N,N'-羰基二咪唑 、 zinc methyl bromide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0~40.0 ℃ 、101.33 kPa 条件下， 反应 49.5h， 生成 methyl (2R,3S)-3-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-3-hydroxy-2-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]propanoate
  参考文献：
  名称：

  Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins

  摘要：

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00460-x