ethyl (3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-2-(4-methylphenylsulfonyloxy)-(2R)-propionate | 918896-35-2

• 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: ethyl (3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-2-(4-methylphenylsulfonyloxy)-(2R)-propionate
• CAS: 918896-35-2
• 化学式: C₂₁H₂₄O₉S
• 分子量: 452.482
• InChiKey: XAMAZRLJGOOYPX-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-2-(4-methylphenylsulfonyloxy)-(2R)-propionate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到ethyl 2-azido-(3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-(2S)-propionate
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056
• 作为产物：
  描述：

  3,4-Methylendioxy-phenyl-formiat 在 盐酸 、 氢氧化钾 、 AD-mix-α 、 正丁基锂 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 53.42h， 生成 ethyl (3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-2-(4-methylphenylsulfonyloxy)-(2R)-propionate
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056