(4S,5S)-3-[(tert-butyloxy)carbonyl]-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-carboxaldehyde | 127306-04-1

• 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: (4S,5S)-3-[(tert-butyloxy)carbonyl]-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-carboxaldehyde
• 英文别名: tert-butyl (4S,5S)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 127306-04-1
• 化学式: C₁₈H₃₁NO₄
• 分子量: 325.448
• InChiKey: XWNYDCXGNOTBAU-LSDHHAIUSA-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：

  (4S,5S)-3-[(tert-butyloxy)carbonyl]-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-carboxaldehyde 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate
  参考文献：
  名称：

  N -Boc-2,2-二甲基恶唑烷-5-甲醛的对映选择性合成，是二肽等排物的多用途前体

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(97)10738-9
• 作为产物：
  描述：

  (3RS,4S)-4-<(tert-butyloxy)carbonyl>-5-(cyclohexylmethyl)-3-hydroxy-1-pentene 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4S,5S)-3-[(tert-butyloxy)carbonyl]-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-carboxaldehyde
  参考文献：
  名称：

  Potent, low molecular weight renin inhibitors containing a C-terminal heterocycle: hydrogen bonding at the active site

  摘要：

  A series of low-nanomolar renin inhibitors containing novel C-terminal heterocycles has been designed by formally cyclizing the C-terminus of a glycol-based inhibitor to the second hydroxyl. Molecular modeling suggests that the heterocyclic oxygen hydrogen bonds as an acceptor to the flap region of renin and that the second hydroxyl in the glycol-based inhibitors behaves similarly.

  DOI：

  10.1021/jm00168a009

文献信息

• Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols
  作者：Alessandro Dondoni、Daniela Perrone、Marilisa Rinaldi

  DOI：10.1021/jo980980u

  日期：1998.12.1

  A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4-diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from beta-amino-alpha-hydroxy aldehydes followed by reduction of the resulting N-benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3-diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV-1 protease inhibitors.
• Peptid-Analoga mit renininhibierender Aktivität
  申请人：MERCK PATENT GmbH

  公开号：EP0446485B1

  公开（公告）日：1995-09-06
• US5401722A
  申请人：——

  公开号：US5401722A

  公开（公告）日：1995-03-28
• Potent, low molecular weight renin inhibitors containing a C-terminal heterocycle: hydrogen bonding at the active site
  作者：Saul H. Rosenberg、Joseph F. Dellaria、Dale J. Kempf、Charles W. Hutchins、Keith W. Woods、Robert G. Maki、Ed De Lara、Kenneth P. Spina、Herman H. Stein

  DOI：10.1021/jm00168a009

  日期：1990.6

  A series of low-nanomolar renin inhibitors containing novel C-terminal heterocycles has been designed by formally cyclizing the C-terminus of a glycol-based inhibitor to the second hydroxyl. Molecular modeling suggests that the heterocyclic oxygen hydrogen bonds as an acceptor to the flap region of renin and that the second hydroxyl in the glycol-based inhibitors behaves similarly.
• 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。