((3S,4R)-4-Benzyloxycarbonyloxy-1,1-difluoro-3-hexanoylamino-undecyl)-phosphonic acid mono-(2-tert-butoxycarbonylamino-ethyl) ester | 866496-39-1

• 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: ((3S,4R)-4-Benzyloxycarbonyloxy-1,1-difluoro-3-hexanoylamino-undecyl)-phosphonic acid mono-(2-tert-butoxycarbonylamino-ethyl) ester
• CAS: 866496-39-1
• 化学式: C₃₂H₅₃F₂N₂O₉P
• 分子量: 678.751
• InChiKey: AVDBJCIAURPKOO-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  46.0
• 可旋转键数：
  22.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  149.49
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((3S,4R)-4-Benzyloxycarbonyloxy-1,1-difluoro-3-hexanoylamino-undecyl)-phosphonic acid mono-(2-tert-butoxycarbonylamino-ethyl) ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到((3S,4R)-4-Benzyloxycarbonyloxy-1,1-difluoro-3-hexanoylamino-undecyl)-phosphonic acid mono-(2-amino-ethyl) ester
  参考文献：
  名称：

  Synthesis of sphingomyelin difluoromethylene analogue

  摘要：

  As a new sphingomyelinase inhibitor, a novel sphingomyelin CF2 analogue was designed and synthesized. One key step of this synthesis is the very mild hydrolysis of the oxazolidinone ring, a suitable intermediate for the introduction of a diethyl difluoromethylphosphonate group, by utilizing the characteristic electron withdrawing nature of the nosyl group at the oxazolidinone ring in an alcoholic solvent to produce the corresponding carbonate attaching at the secondary hydroxy group. The synthesized CF2 analogue inactivated toward B. cereus sphingomyelinase with nearly the same attitude as the nitrogen analogue that we previously reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.018
• 作为产物：
  描述：

  benzyl [(3S,4R)-1-[diethoxy(oxido)phosphaniumyl]-1,1-difluoro-3-(hexanoylamino)undecan-4-yl] carbonate 在 三甲基溴硅烷 、 三氯乙腈 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 ((3S,4R)-4-Benzyloxycarbonyloxy-1,1-difluoro-3-hexanoylamino-undecyl)-phosphonic acid mono-(2-tert-butoxycarbonylamino-ethyl) ester
  参考文献：
  名称：

  Synthesis of sphingomyelin difluoromethylene analogue

  摘要：

  As a new sphingomyelinase inhibitor, a novel sphingomyelin CF2 analogue was designed and synthesized. One key step of this synthesis is the very mild hydrolysis of the oxazolidinone ring, a suitable intermediate for the introduction of a diethyl difluoromethylphosphonate group, by utilizing the characteristic electron withdrawing nature of the nosyl group at the oxazolidinone ring in an alcoholic solvent to produce the corresponding carbonate attaching at the secondary hydroxy group. The synthesized CF2 analogue inactivated toward B. cereus sphingomyelinase with nearly the same attitude as the nitrogen analogue that we previously reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.018