tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate | 117997-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate
• 英文别名: 3-tert-butyloxycarbonyl-4S-cyclohexylmethyl-2,2-dimethyl-5R-oxazolidinyl carboxaldehyde；t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate；tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 117997-58-7
• 化学式: C₁₈H₃₁NO₄
• 分子量: 325.448
• InChiKey: XWNYDCXGNOTBAU-GJZGRUSLSA-N

物化性质

• 沸点：
  414.8±45.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate 在 ethandithiol 、 ruthenium trichloride 、 diethylphosphoryl cyanide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 过碘酸 、 N,N-二异丙基乙胺 、 乙酰氯 、 三氟乙酸 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 35.25h， 生成 (2R,3R,4R,5S)-6-Cyclohexyl-3,4-dihydroxy-5-{(S)-3-(1H-imidazol-4-yl)-2-[2-(naphthalen-1-yloxy)-acetylamino]-propionylamino}-2-isopropyl-hexanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide
  参考文献：
  名称：

  Inhibitors of the protease from human immunodeficiency virus: design and modeling of a compound containing a dihydroxyethylene isostere insert with high binding affinity and effective antiviral activity

  摘要：

  The peptidomimetic template and the dihydroxyethylene isostere insert that were applied successfully to the design of renin inhibitors have been extended to the related protease from human immunodeficiency virus (HIV). The present report describes the structure-activity study leading to the identification of an inhibitor with a K(i) of < 1 nM for the HIV type-1 protease (compound II). This compound, containing a diol insert, is highly effective in blocking polyprotein processing in in vitro cell culture assays. Results obtained from kinetic analysis, studies of the stereochemistry of the insert, and modeling have led to insights as to the requisites involved in the active site-inhibitor interaction.

  DOI：

  10.1021/jm00112a005
• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-1-环己基-3-氧代-2-丙基]氨基甲酸酯 在 ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 三乙胺 、 N,N'-羰基二咪唑 、 zinc dibromide 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate
  参考文献：
  名称：

  （2S，4S，5S）-5-氨基-6-环己基-4-羟基-2-异丙基己酸正丁基酰胺的羟乙烯二肽异戊烯的合成

  摘要：

  描述了由Boc-L-苯丙氨酸立体选择性地合成（2S，4S，5S）-5-氨基-6-环己基-4-羟基-2-异丙基己酸正丁基酰胺的羟基亚乙基二肽等排体。

  DOI：

  10.1016/s0040-4039(00)91634-4

文献信息

• Amino acid derivatives having renin inhibiting activity
  申请人：Hoffmann La Roche Inc.

  公开号：US05688946A1

  公开（公告）日：1997-11-18

  The compounds of the formula ##STR1## in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency.

  上述化学公式##STR1##的化合物，以光学纯的立体异构体、立体异构体混合物、立体异构体对映体混合物或立体异构体对映体混合物的形式，以及它们的药用盐，都能抑制天然酶肾素的活动，因此可以以药物制剂的形式用于控制或预防高血压和心功能不全。
• New approaches to the asymmetric synthesis of dipeptide isosteres via β-Lactam Synthon Method
  作者：Iwao Ojima、Hong Wang、Tao Wang、Edward W. Ng

  DOI：10.1016/s0040-4039(97)10677-3

  日期：1998.2

  New and efficient synthetic routes to dipeptide isosteres with high enantiomeric purity, e.g., hydroxyethylene, dihydroxyethylene and hydroxyethylamine isosteres, have been developed via oxiranes 6 and formyloxazolines 13 derived from N-t-Boc-β-lactams 4.

  通过由N -t-Boc-β-内酰胺4衍生的肟基6和甲酰恶唑啉13，已经开发出具有高对映体纯度的二肽等排体（例如，羟乙烯，二羟乙烯和羟乙胺等排体）的新型有效合成途径。
• Enantioselective synthesis of N-Boc-2,2-dimethyloxazolidine-5-carbaldehydes, versatile precursors of dipeptide isosteres
  作者：Mireia Pastó、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1016/s0040-4039(97)10738-9

  日期：1998.3

  2-dimethyl-oxazolidine-5-carbaldehydes have been efficiently prepared from N-Boc-3-amino-1,2-alkanediols, readily available in enantiopure or enantioenriched form by Sharpless epoxidation methodology. These compounds have been converted into N-Boc-(S)-γ-[(S)-1-aminoalkyl]-γ-lactones which are key intermediates of hydroxyethylene dipeptide isosteres.

  高度对映体富集的顺式和反式N -Boc-2,2-二甲基-恶唑烷-5-甲醛是由N -Boc-3-氨基-1,2-链烷二醇有效制备的，可通过Sharpless环氧化方法轻松地以对映体或对映体形式获得。这些化合物已被转化为N- Boc-（S）-γ -[（（S）-1-氨基烷基）-γ-内酯，它们是羟乙烯二肽等排体的关键中间体。
• Stereoselective synthesis of a C-terminal component of renin inhibitors via iterative homologation
  作者：Adalbert Wagner、Martina Mollath

  DOI：10.1016/s0040-4039(00)61634-9

  日期：1993.1

  A stereoselective synthesis of an aminodiol derivative (dipeptide mimic) has been developed via iterative homologation of protected cyclohexylalaninal (Dondoni reaction).

  通过对受保护的环己基丙氨酸进行重复同源化（Dondoni反应），开发了氨基二醇衍生物（二肽模拟物）的立体选择性合成方法。
• Renin inhibiting peptides with polar end groups
  申请人：THE UPJOHN COMPANY

  公开号：EP0329295A1

  公开（公告）日：1989-08-23

  The present invention provides novel renin-inhibiting peptides having a noncleavable transition state insert corresponding to the 10,11- position of the renin substrate (angiotensinogen) and a polyhydroxy-substituted alkyl moiety bonded directly through carbon or nitrogen to the N-terminus. Such inhibitors are useful for the diagnosis and control of renin-dependent hypertension and other related diseases.

  本发明提供了具有与肾素底物（血管紧张素原）的10,11-位置对应的不可切割过渡态插入物的新型抑制肾素的肽，以及通过碳或氮直接与N-末端结合的多羟基取代烷基基团。这些抑制剂对于诊断和控制肾素依赖性高血压和其他相关疾病非常有用。