[(2S)-hydroxy-(1R)-hydroxymethyl-2-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-ethyl]-carbamic acid tert-butyl ester | 918896-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: [(2S)-hydroxy-(1R)-hydroxymethyl-2-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S,2R)-1,3-dihydroxy-1-(6-methoxy-7-methyl-1,3-benzodioxol-5-yl)propan-2-yl]carbamate
• CAS: 918896-37-4
• 化学式: C₁₇H₂₅NO₇
• 分子量: 355.388
• InChiKey: RLFZWFANKTWICK-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S)-hydroxy-(1R)-hydroxymethyl-2-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-ethyl]-carbamic acid tert-butyl ester 、 2,2-二甲氧基丙烷 在 camphor-10-sulfonic acid 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以90%的产率得到[[(4S)-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-2,2-dimethyl[1,3]dioxan-(5R)-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：

  3,4-Methylendioxy-phenyl-formiat 在 盐酸 、 氢氧化钾 、 AD-mix-α 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium azide 、 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 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 69.42h， 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

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.