(1R,2S,3S,5R)-2-aminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol | 1000337-22-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,3S,5R)-2-aminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
• 英文别名: (1R,2S,3S,5R)-2-(aminomethyl)-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
• CAS: 1000337-22-3
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: GAKMHQXAPOPLBA-BDNRQGISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-二氯-5-氨基嘧啶 、 (1R,2S,3S,5R)-2-aminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 以59%的产率得到(1R,2S,3S,5R)-2-[(5-amino-6-chloropyrimidin-4-ylamino)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
  参考文献：
  名称：

  Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

  摘要：

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.054
• 作为产物：
  描述：

  (1R,2S,3S,5R)-2-(azidomethyl)-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以92%的产率得到(1R,2S,3S,5R)-2-aminomethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol
  参考文献：
  名称：

  Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

  摘要：

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.054

文献信息

• Synthesis and application of monoterpene-based chiral aminodiols
  作者：Zsolt Szakonyi、Anasztázia Hetényi、Ferenc Fülöp

  DOI：10.1016/j.tet.2007.07.065

  日期：2008.2

  Primary, secondary and tertiary aminodiols were synthetized regio- and stereoselectively from (-)-alpha-pinene 1 via a-pinene oxide 2, (-)-trans-pinocarveol 3 and key intermediate epoxy alcohol 4. N-Benzyl derivative 5 was transformed to spiro-fused oxazolidine 13 in a highly regioselective ring closure. Aminodiols and their derivatives 5-13 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde, resulting in chiral 1-phenyl- 1-propanol. The substituent effect on the nitrogen was studied in detail and the best enantioselectivity was observed in the case of N-methyl-N-benzyl-substituted derivative 8. The phenomenon was interpreted by using molecular modelling at an ab initio level. (c) 2007 Elsevier Ltd. All rights reserved.