ethyl (4R,5S)-5-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxy-5-methylphenyl]-2-oxo-1,3,2-dioxathiolane-4-carboxylate | 1026340-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (4R,5S)-5-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxy-5-methylphenyl]-2-oxo-1,3,2-dioxathiolane-4-carboxylate
• CAS: 1026340-65-7
• 化学式: C₁₉H₃₀O₇SSi
• 分子量: 430.595
• InChiKey: GMALTLNLJJEBSN-KRXSAHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  99.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (4R,5S)-5-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxy-5-methylphenyl]-2-oxo-1,3,2-dioxathiolane-4-carboxylate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以0.3 g的产率得到ethyl (3R)-azido-3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-(2R)-hydroxy-propionic acid ethyl 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：

  2-甲基苯甲醚 在 咪唑 、 盐酸 、 AD-mix-α 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 对甲苯磺酸 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 65.5h， 生成 ethyl (4R,5S)-5-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxy-5-methylphenyl]-2-oxo-1,3,2-dioxathiolane-4-carboxylate
  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

文献信息

• Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions
  作者：S. Chandrasekhar、N. Ramakrishna Reddy、Y. Srinivasa Rao

  DOI：10.1016/j.tet.2006.09.056

  日期：2006.12

  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.