(Z)-N-<(4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-isopropyl-5-methylenyl-1,3-oxazolidinyl>benzylamine N-oxide | 219586-52-4

• 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: (Z)-N-<(4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-isopropyl-5-methylenyl-1,3-oxazolidinyl>benzylamine N-oxide
• 英文别名: N-benzyl-1-[(4S,5R)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-(2-methylpropyl)-1,3-oxazolidin-5-yl]methanimine oxide
• CAS: 219586-52-4
• 化学式: C₂₂H₃₄N₂O₄
• 分子量: 390.523
• InChiKey: IYRPLDINGRQDFW-BWYCHMBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methylallylmagnesium Chloride 、 (Z)-N-<(4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-isopropyl-5-methylenyl-1,3-oxazolidinyl>benzylamine N-oxide 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (4S,5R,6S)-4-N-benzylhydroxylamine-6-tert-butoxycarbonylamino-6N,5O-isopropylidene-8-methyl-2-vinyl-5-nonanol 、 (4R,5R,6S)-4-N-benzylhydroxylamine-6-tert-butoxycarbonylamino-6N,5O-isopropylidene-8-methyl-2-vinyl-5-nonanol
  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：

  (2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methyl-1-(2-thiazolyl)-1-pentanol 在 4-甲基苯磺酸吡啶 、 magnesium sulfate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.5h， 生成 (Z)-N-<(4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-isopropyl-5-methylenyl-1,3-oxazolidinyl>benzylamine N-oxide
  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

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.