methyl (3R,4R)-4-(1,4,5,6-tetramethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate | 1526958-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (3R,4R)-4-(1,4,5,6-tetramethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate
• 英文别名: methyl 2-[(4R,5R)-2,2-dimethyl-5-(1,4,5,6-tetramethoxynaphthalen-2-yl)-1,3-dioxolan-4-yl]acetate
• CAS: 1526958-34-8
• 化学式: C₂₂H₂₈O₈
• 分子量: 420.46
• InChiKey: YIPSQKBFBPCIGT-OXQOHEQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R)-4-(1,4,5,6-tetramethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate 在 盐酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以87%的产率得到(4R,5R)-4-hydroxy-5-(1,4,5,6-tetramethoxynaphth-2-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A concise total synthesis of arizonins B1 and C1

  摘要：

  A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.011
• 作为产物：
  描述：

  methyl (3R,4R)-4-(1-hydroxy-4,5,6-trimethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.33h， 以85%的产率得到methyl (3R,4R)-4-(1,4,5,6-tetramethoxynaphthalen-2-yl)-3,4-isopropylidenedioxybutanoate
  参考文献：
  名称：

  A concise total synthesis of arizonins B1 and C1

  摘要：

  A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.011

文献信息

• A concise total synthesis of arizonins B1 and C1
  作者：Rodney A. Fernandes、Sandip V. Mulay、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2013.10.011

  日期：2013.12

  A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.