2-<(4S,5S)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole | 219586-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-<(4S,5S)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole
• 英文别名: tert-butyl (4S,5S)-4-(cyclohexylmethyl)-2,2-dimethyl-5-(1,3-thiazol-2-yl)-1,3-oxazolidine-3-carboxylate
• CAS: 219586-46-6
• 化学式: C₂₀H₃₂N₂O₃S
• 分子量: 380.552
• InChiKey: HESPDTYSBSDZSA-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<(4S,5S)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole 在 palladium dihydroxide 盐酸 、 氢气 、 氯化二乙基铝 、 magnesium sulfate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， -78.0~90.0 ℃ 、303.98 kPa 条件下， 反应 24.5h， 生成 (2R,3s,4S)-2,4-diamino-1,5-dicyclohexyl-3-pentanol
  参考文献：
  名称：

  Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols

  摘要：

  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.

  DOI：

  10.1021/jo980980u
• 作为产物：
  描述：

  2-甲氧基丙烯 、 tert-butyl N-[(2S)-3-cyclohexyl-1-hydroxy-1-(1,3-thiazol-2-yl)propan-2-yl]carbamate 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以72%的产率得到2-<(4S,5R)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole
  参考文献：
  名称：

  Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols

  摘要：

  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.

  DOI：

  10.1021/jo980980u