(R)-2-Benzyl-3-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-isoxazolidin-5-one | 161561-87-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-2-Benzyl-3-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-isoxazolidin-5-one
• 英文别名: (3R)-2-benzyl-3-[(2S)-3-[tert-butyl(diphenyl)silyl]oxy-2-hydroxypropyl]-1,2-oxazolidin-5-one
• CAS: 161561-87-1
• 化学式: C₂₉H₃₅NO₄Si
• 分子量: 489.687
• InChiKey: MOGQIJFCIFWKPX-RPBOFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-Benzyl-3-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-isoxazolidin-5-one 在 potassium carbonate 作用下， 生成 [(3R,5R)-2-Benzyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-isoxazolidin-3-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Stereocontrolled entry to negamycin from d-glucose

  摘要：

  Conjugate addition-rearrangement of N-benzylhydroxy-lamine to lactone 6 provides isoxazolidin-5-one 7 which was in turn mesylated at the hydroxy group and subjected to the next skeleton rearrangement to afford 3,5-disubstituted isoxazolidine 10. Standard transformation of 10 gave negamycin lactone 4.

  DOI：

  10.1016/0040-4039(94)02194-g
• 作为产物：
  描述：

  N-苄基羟胺 、 (S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-5,6-dihydro-2Hpyran-2-one 以 乙醇 为溶剂， 反应 1.0h， 生成 (R)-2-Benzyl-3-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-isoxazolidin-5-one
  参考文献：
  名称：

  Stereocontrolled entry to negamycin from d-glucose

  摘要：

  Conjugate addition-rearrangement of N-benzylhydroxy-lamine to lactone 6 provides isoxazolidin-5-one 7 which was in turn mesylated at the hydroxy group and subjected to the next skeleton rearrangement to afford 3,5-disubstituted isoxazolidine 10. Standard transformation of 10 gave negamycin lactone 4.

  DOI：

  10.1016/0040-4039(94)02194-g

文献信息

• Stereocontrolled entry to negamycin from d-glucose
  作者：Darlusz Socha、Margarita Jurczak、Marek Chmielewski

  DOI：10.1016/0040-4039(94)02194-g

  日期：1995.1

  Conjugate addition-rearrangement of N-benzylhydroxy-lamine to lactone 6 provides isoxazolidin-5-one 7 which was in turn mesylated at the hydroxy group and subjected to the next skeleton rearrangement to afford 3,5-disubstituted isoxazolidine 10. Standard transformation of 10 gave negamycin lactone 4.