(3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone | 172293-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone
• 英文别名: (3R,4S,5R)-6-[tert-butyl(diphenyl)silyl]oxy-1-(1,3-thiazol-2-yl)-3,4,5-tris(trimethylsilyloxy)hexan-1-one
• CAS: 172293-75-3
• 化学式: C₃₄H₅₅NO₅SSi₄
• 分子量: 702.222
• InChiKey: UHKAIXVLDKENBF-IWWXRALLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone 在 4 A molecular sieve 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.42h， 生成 2-[(4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran-2-yl]-3-methyl-thiazol-3-ium
  参考文献：
  名称：

  Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

  摘要：

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.

  DOI：

  10.1021/jo00127a047
• 作为产物：
  描述：

  (3R,4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide 在 吡啶 、 正丁基锂 、 六甲基二硅氮烷 作用下， 以 乙醚 为溶剂， 反应 3.42h， 生成 (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone
  参考文献：
  名称：

  Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

  摘要：

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.

  DOI：

  10.1021/jo00127a047

文献信息

• Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative
  作者：Gerard Devianne、Jean-Marc Escudier、Michel Baltas、Liliane Gorrichon

  DOI：10.1021/jo00127a047

  日期：1995.11

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.