methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-methylenedecanoate | 1170688-92-2

• 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-methylenedecanoate
• 英文别名: methyl (2R,3S)-3-[[(S)-tert-butylsulfinyl]amino]-6-methylidene-2-[(2S)-1-phenylmethoxypropan-2-yl]decanoate
• CAS: 1170688-92-2
• 化学式: C₂₆H₄₃NO₄S
• 分子量: 465.698
• InChiKey: YMWKAEGCNXUNLY-WSMWIHCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-methylenedecanoate 在 盐酸 、 水 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以93%的产率得到methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-tert-butoxycarbonylamino-6-methylenedecanoate
  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-methyleneoctanimine 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72%的产率得到methyl (2R,3S)-2-[(S)-2-benzyloxy-1-methylethyl]-3-[(S(S))-tert-butylsulfinylamino]-6-methylenedecanoate
  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

文献信息

• An approach to an asymmetric synthesis of stemofoline
  作者：Eric J. Thomas、Clare F. Vickers

  DOI：10.1016/j.tetasy.2009.03.002

  日期：2009.5

  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.