(S)-3-Benzyloxy-3-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-thiazol-2-yl-propan-1-one | 136029-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-Benzyloxy-3-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-thiazol-2-yl-propan-1-one
• CAS: 136029-19-1
• 化学式: C₂₃H₂₉NO₆S
• 分子量: 447.552
• InChiKey: YXWZABBCLNZDHV-MTQWCTHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.11
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (S)-3-Benzyloxy-3-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-thiazol-2-yl-propan-1-one 在 盐酸 作用下， 反应 2.0h， 以25%的产率得到methyl 3-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-gluco-heptopyranoside
  参考文献：
  名称：

  Stereoselective construction of polyhydroxyalkyl 2-thiazolyl ketones (thiazole ketoses) from d-glyceraldehyde and d-arabinose acetonides by wittig-michael sequence. a route to d-gluco-KDO

  摘要：

  The carbonylolefination of the title alkoxy aldehydes by 2-thiazolecarbonylmethylenetriphenyl-phosphorane 3 affords the corresponding (E)-enones which undergo syn-diastereoselective (ds, 85-95%) 1,4-conjugate addition of benzyl oxide anion; acid-catalyzed methanolysis of polyalkoxyalkyl ketones obtained in that way gives methyl 1-(2-thiazolyl)pyranoside precursors to ulosonic acids.

  DOI：

  10.1016/s0040-4039(00)79735-8
• 作为产物：
  描述：

  1-(thiazol-2-yl)-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one 以 四氢呋喃 、 苯 为溶剂， 反应 27.0h， 生成 (S)-3-Benzyloxy-3-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-thiazol-2-yl-propan-1-one
  参考文献：
  名称：

  Stereoselective construction of polyhydroxyalkyl 2-thiazolyl ketones (thiazole ketoses) from d-glyceraldehyde and d-arabinose acetonides by wittig-michael sequence. a route to d-gluco-KDO

  摘要：

  The carbonylolefination of the title alkoxy aldehydes by 2-thiazolecarbonylmethylenetriphenyl-phosphorane 3 affords the corresponding (E)-enones which undergo syn-diastereoselective (ds, 85-95%) 1,4-conjugate addition of benzyl oxide anion; acid-catalyzed methanolysis of polyalkoxyalkyl ketones obtained in that way gives methyl 1-(2-thiazolyl)pyranoside precursors to ulosonic acids.

  DOI：

  10.1016/s0040-4039(00)79735-8