methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-oxodecanoate ethylene acetal | 1170688-87-5

• 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)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-oxodecanoate ethylene acetal
• CAS: 1170688-87-5
• 化学式: C₂₇H₄₅NO₆S
• 分子量: 511.723
• InChiKey: IOWXHJIRXLVPQZ-ZDCNHDKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  35.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-oxodecanoate ethylene acetal 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 以91.5%的产率得到(2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-oxodecan-1-ol ethylene acetal
  参考文献：
  名称：

  An approach to an asymmetric synthesis of stemofoline

  摘要：

  A stereoselective Mannich reaction between an (S)-tert-butylsulfinimine and methyl (S)-4-benzyloxy-3-methylbutanoate followed by treatment with acid and N-protection was used to prepare methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-tert-butoxycarbonylamino-6-methylenedecanoate. This was taken through to methyl (4R,5S)-4-[(S)-2-benzyloxy-1-methylethyl]-5-tert-butoxycarbonylamino-3,8-dioxododecanoate which on treatment with trifluoroacetic acid cyclised stereoselectively to give (1R,2S,4R,5S)-4-[(S)-2-benzyloxy-1-methylethyl]-1-butyl-2-methoxycarbonyl-8-tert-butoxycarbonyl-3-oxo-8-azabicyclo[3.2.1]octane, a potential precursor of stemofoline. Reduction and N-deprotection of this ketone gave (1R,2S,3R,4R,5S)-4-[(S)-2-benzyloxy-1-methylethyl]-1-butyl-2-methoxycarbonyl-8-azabicyclo[3.2.1]octan-3-ol the structure of which was confirmed by X-ray diffraction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.002
• 作为产物：
  描述：

  methyl (S)-4-(benzyloxy)-3-methylbutanoate 、 (S(S))-N-(tert-butylsulfinyl)-4-oxooctanimine ethyleneacetal 在 lithium diisopropyl amide 、 三异丙氧基氯化钛 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以66%的产率得到methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-oxodecanoate ethylene acetal
  参考文献：
  名称：

  An approach to an asymmetric synthesis of stemofoline

  摘要：

  A stereoselective Mannich reaction between an (S)-tert-butylsulfinimine and methyl (S)-4-benzyloxy-3-methylbutanoate followed by treatment with acid and N-protection was used to prepare methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-tert-butoxycarbonylamino-6-methylenedecanoate. This was taken through to methyl (4R,5S)-4-[(S)-2-benzyloxy-1-methylethyl]-5-tert-butoxycarbonylamino-3,8-dioxododecanoate which on treatment with trifluoroacetic acid cyclised stereoselectively to give (1R,2S,4R,5S)-4-[(S)-2-benzyloxy-1-methylethyl]-1-butyl-2-methoxycarbonyl-8-tert-butoxycarbonyl-3-oxo-8-azabicyclo[3.2.1]octane, a potential precursor of stemofoline. Reduction and N-deprotection of this ketone gave (1R,2S,3R,4R,5S)-4-[(S)-2-benzyloxy-1-methylethyl]-1-butyl-2-methoxycarbonyl-8-azabicyclo[3.2.1]octan-3-ol the structure of which was confirmed by X-ray diffraction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.002