ethyl 2-azido-(3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-(2S)-propionate | 918896-36-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-azido-(3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-(2S)-propionate
• 英文别名: ethyl (2S,3S)-2-azido-3-hydroxy-3-(6-methoxy-7-methyl-1,3-benzodioxol-5-yl)propanoate
• CAS: 918896-36-3
• 化学式: C₁₄H₁₇N₃O₆
• 分子量: 323.305
• InChiKey: ZCUZJDFRGDLRHG-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-azido-(3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-(2S)-propionate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 [(2S)-hydroxy-(1R)-hydroxymethyl-2-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-ethyl]-carbamic acid tert-butyl ester
  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：

  ethyl (2R,3S)-dihydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl) propionate 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 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