benzyl [(3S,4R)-1-[diethoxy(oxido)phosphaniumyl]-1,1-difluoro-3-(hexanoylamino)undecan-4-yl] carbonate | 866496-37-9

• 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: benzyl [(3S,4R)-1-[diethoxy(oxido)phosphaniumyl]-1,1-difluoro-3-(hexanoylamino)undecan-4-yl] carbonate
• CAS: 866496-37-9
• 化学式: C₂₉H₄₈F₂NO₇P
• 分子量: 591.673
• InChiKey: JJTTZKNZAZJJBF-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  40
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,3R)-2,3-epoxy-1-decanol 在 palladium on activated charcoal 咪唑 、 2,6-二甲基吡啶 、 盐酸 、 六甲基磷酰三胺 、 正丁基锂 、 sodium azide 、 ammonium cerium(IV) nitrate 、 18-冠醚-6 、 水 、 氢气 、 双氧水 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 、 苯硫酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 benzyl [(3S,4R)-1-[diethoxy(oxido)phosphaniumyl]-1,1-difluoro-3-(hexanoylamino)undecan-4-yl] carbonate
  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

文献信息

• Synthesis of sphingomyelin difluoromethylene analogue
  作者：Toshikazu Hakogi、Tetsuya Yamamoto、Shinobu Fujii、Kiyoshi Ikeda、Shigeo Katsumura

  DOI：10.1016/j.tetlet.2006.02.018

  日期：2006.4

  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.