tert-butyl N-[(2S,3S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolan-3-yl]carbamate | 192824-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl N-[(2S,3S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolan-3-yl]carbamate
• CAS: 192824-02-5
• 化学式: C₁₇H₃₃NO₅Si
• 分子量: 359.538
• InChiKey: IWVGFHLPASTTFC-SGMGOOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolan-3-yl]carbamate 在 二异丁基氢化铝 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.75h， 生成 3-benzoylamino-2,3,6-trideoxy-β-L-lyxo-hexose
  参考文献：
  名称：

  A New Route to 3-Amino Sugars. A Concise Synthesis of l-Daunosamine and d-Ristosamine Derivatives

  摘要：

  An asymmetric aldol strategy has been developed for the synthesis of L-daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O-TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two-step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similarly, lactone 32 was converted to N-benzoylristosamide 42 with an overall yield of 18% starting from 12.

  DOI：

  10.1021/jo970576f
• 作为产物：
  描述：

  (S)-2-(叔丁基-二甲基-锡氧基)-丙醛 在 lithium hydroxide 、 二苯基磷酸 、 双氧水 、 4-甲基苯磺酸吡啶 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 31.33h， 生成 tert-butyl N-[(2S,3S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolan-3-yl]carbamate
  参考文献：
  名称：

  A New Route to 3-Amino Sugars. A Concise Synthesis of l-Daunosamine and d-Ristosamine Derivatives

  摘要：

  An asymmetric aldol strategy has been developed for the synthesis of L-daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O-TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two-step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similarly, lactone 32 was converted to N-benzoylristosamide 42 with an overall yield of 18% starting from 12.

  DOI：

  10.1021/jo970576f

文献信息

• A New Route to 3-Amino Sugars. A Concise Synthesis of <scp>l</scp>-Daunosamine and <scp>d</scp>-Ristosamine Derivatives
  作者：Mukund P. Sibi、Jianliang Lu、Jessica Edwards

  DOI：10.1021/jo970576f

  日期：1997.8.1

  An asymmetric aldol strategy has been developed for the synthesis of L-daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O-TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two-step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similarly, lactone 32 was converted to N-benzoylristosamide 42 with an overall yield of 18% starting from 12.