benzyl N-methyl-N-[(1S,3R,8S,10R,11R,12R,13R,14S)-5-methyl-11-[methyl(phenylmethoxycarbonyl)amino]-7-oxo-8,12,14-tris(trimethylsilyloxy)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradec-5-en-13-yl]carbamate | 134694-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl N-methyl-N-[(1S,3R,8S,10R,11R,12R,13R,14S)-5-methyl-11-[methyl(phenylmethoxycarbonyl)amino]-7-oxo-8,12,14-tris(trimethylsilyloxy)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradec-5-en-13-yl]carbamate
• CAS: 134694-97-6
• 化学式: C₃₉H₅₈N₂O₁₁Si₃
• 分子量: 815.153
• InChiKey: JGSLYFSLUSIKNH-BLVSWUOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl N-methyl-N-[(1S,3R,8S,10R,11R,12R,13R,14S)-5-methyl-11-[methyl(phenylmethoxycarbonyl)amino]-7-oxo-8,12,14-tris(trimethylsilyloxy)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradec-5-en-13-yl]carbamate 在 盐酸 、 tris(dibenzylideneacetone)dipalladium (0) 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 反应 3.5h， 生成 [(4aR,5S,6S,7R,8S,8aR,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-4a,6,8-trihydroxy-2-methyl-4-oxo-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester
  参考文献：
  名称：

  Oxidation and alkylation of spectinomycin derivatives: synthesis of trospectomycin from spectinomycin

  摘要：

  Trospectomycin can be prepared in five steps from spectinomycin. The overall yield of the process is 13.3%. The synthesis involves a new oxidation of silyl enol ether 4 to enone 5 by use of an alkyl hydroperoxide. This reaction is mild and very selective, giving excellent yields. The synthesis also involves a gamma-alkylation of enone 5 activated by a beta-oxygen. This alkylation is unusual in that no alkylation is seen at the a (4') carbon.

  DOI：

  10.1021/jo00055a021
• 作为产物：
  描述：

  bis-Cbz-spectinomycin 在 叔丁基过氧化氢 、 三乙胺 、 copper dichloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 benzyl N-methyl-N-[(1S,3R,8S,10R,11R,12R,13R,14S)-5-methyl-11-[methyl(phenylmethoxycarbonyl)amino]-7-oxo-8,12,14-tris(trimethylsilyloxy)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradec-5-en-13-yl]carbamate
  参考文献：
  名称：

  Oxidation and alkylation of spectinomycin derivatives: synthesis of trospectomycin from spectinomycin

  摘要：

  Trospectomycin can be prepared in five steps from spectinomycin. The overall yield of the process is 13.3%. The synthesis involves a new oxidation of silyl enol ether 4 to enone 5 by use of an alkyl hydroperoxide. This reaction is mild and very selective, giving excellent yields. The synthesis also involves a gamma-alkylation of enone 5 activated by a beta-oxygen. This alkylation is unusual in that no alkylation is seen at the a (4') carbon.

  DOI：

  10.1021/jo00055a021

文献信息

• Oxidation and alkylation of spectinomycin derivatives: synthesis of trospectomycin from spectinomycin
  作者：Paul M. Herrinton、Karen L. Klotz、William M. Hartley

  DOI：10.1021/jo00055a021

  日期：1993.1

  Trospectomycin can be prepared in five steps from spectinomycin. The overall yield of the process is 13.3%. The synthesis involves a new oxidation of silyl enol ether 4 to enone 5 by use of an alkyl hydroperoxide. This reaction is mild and very selective, giving excellent yields. The synthesis also involves a gamma-alkylation of enone 5 activated by a beta-oxygen. This alkylation is unusual in that no alkylation is seen at the a (4') carbon.