ethyl N-[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]carbamate | 156540-64-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]carbamate
• CAS: 156540-64-6
• 化学式: C₁₇H₃₃NO₄
• 分子量: 315.453
• InChiKey: YYXMQLLVOVBCTI-HRCADAONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]carbamate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以5.1 kg的产率得到(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane
  参考文献：
  名称：

  Unique and Efficient Synthesis of [2S-(2R*,3S*,4R*)]-2-Amino-1-cyclohexyl- 6-methyl-3,4-heptanediol, a Popular C-Terminal Component of Many Renin Inhibitors

  摘要：

  DOI：

  10.1021/jo960694n
• 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 盐酸 、 4-二甲氨基吡啶 、 四氧化锇 、 potassium tert-butylate 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 异丙醇 、 甲苯 为溶剂， 反应 28.0h， 生成 ethyl N-[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]carbamate
  参考文献：
  名称：

  Diastereoselectivity in the osmium-catalyzed dihydroxylation of allylic amides and carbamates

  摘要：

  The stereochemistry of the osmium-catalyzed dihydroxylation of a series of chiral allylic amides and carbamates has been studies. The diastereoselectivity of these reactions was found to be dependent upon the solvent and the nitrogen protecting group as well as the geometry and substitution pattern of the olefin substrate. In contrast to the erythro selectivity observed with allylic alcohols, osmylations of the allylic amides and carbamates in this study were threo selective. Stoichiometric osmylations were consistently more selective than the corresponding catalytic reactions. Control experiments suggest this is due to the presence of a second catalytic cycle based upon an osmium glycolate catalyst which accumulates as the reaction proceeds to completion. Double diastereoselective dihydroxylations of allylic carbamates were also briefly examined.

  DOI：

  10.1016/0957-4166(94)80024-3

文献信息

• Unique and Efficient Synthesis of [2<i>S</i>-(2<i>R</i>*,3<i>S</i>*,4<i>R</i>*)]-2-Amino-1-cyclohexyl- 6-methyl-3,4-heptanediol, a Popular C-Terminal Component of Many Renin Inhibitors
  作者：Mark A. Schwindt、Daniel T. Belmont、Mark Carlson、Lloyd C. Franklin、Valerie S. Hendrickson、Gregory L. Karrick、Russell W. Poe、Denis M. Sobieray、Jim Van De Vusse

  DOI：10.1021/jo960694n

  日期：1996.1.1
• Diastereoselectivity in the osmium-catalyzed dihydroxylation of allylic amides and carbamates
  作者：Damian J. Krysan、Todd W. Rockway、Anthony R. Haight

  DOI：10.1016/0957-4166(94)80024-3

  日期：1994.4

  The stereochemistry of the osmium-catalyzed dihydroxylation of a series of chiral allylic amides and carbamates has been studies. The diastereoselectivity of these reactions was found to be dependent upon the solvent and the nitrogen protecting group as well as the geometry and substitution pattern of the olefin substrate. In contrast to the erythro selectivity observed with allylic alcohols, osmylations of the allylic amides and carbamates in this study were threo selective. Stoichiometric osmylations were consistently more selective than the corresponding catalytic reactions. Control experiments suggest this is due to the presence of a second catalytic cycle based upon an osmium glycolate catalyst which accumulates as the reaction proceeds to completion. Double diastereoselective dihydroxylations of allylic carbamates were also briefly examined.