(2R,3R,4R,5R)-1-(4-methoxybenzyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(but-3-enyl) pyrrolidine | 1382680-65-0

• 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: (2R,3R,4R,5R)-1-(4-methoxybenzyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(but-3-enyl) pyrrolidine
• 英文别名: (2R,3R,4R,5R)-2-but-3-enyl-1-[(4-methoxyphenyl)methyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine
• CAS: 1382680-65-0
• 化学式: C₃₈H₄₃NO₄
• 分子量: 577.764
• InChiKey: AVRRPISOLNMRRQ-SIMZDOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-1-(4-methoxybenzyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(but-3-enyl) pyrrolidine 在 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以73%的产率得到4-((2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-(4-methoxybenzyl)pyrrolidin-2-yl)butan-2-one
  参考文献：
  名称：

  A concise and divergent approach to radicamine B and hyacinthacine A3 based on a step-economic transformation

  摘要：

  Based on our recently developed step-economic methodology of reductive alkylation of lactams/amides, we have developed a two-step synthesis of azasugar radicamine B (2a) and a four-step synthesis of azasugar hyacinthacine A(3) (5) from the common chiral building block 12. Hantzsch ester (HEH) was used as a milder hydride donor in the one-pot stereoselective reductive alkylation of lactam 12. The Wacker oxidation of fully substituted pyrrolidine derivative 2,5-trans-17 led to the synthesis of hyacinthacine A(3) (5). Compound 2,5-trans-17 could also serve as a plausible key intermediate for the synthesis of broussonetine sub-class of azasugars. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.085
• 作为产物：
  描述：

  (3S,4R,5R)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one 、 3-Butenylmagnesium bromide 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 二氢吡啶 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 2.75h， 以53%的产率得到(2R,3R,4R,5R)-1-(4-methoxybenzyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(but-3-enyl) pyrrolidine
  参考文献：
  名称：

  A concise and divergent approach to radicamine B and hyacinthacine A3 based on a step-economic transformation

  摘要：

  Based on our recently developed step-economic methodology of reductive alkylation of lactams/amides, we have developed a two-step synthesis of azasugar radicamine B (2a) and a four-step synthesis of azasugar hyacinthacine A(3) (5) from the common chiral building block 12. Hantzsch ester (HEH) was used as a milder hydride donor in the one-pot stereoselective reductive alkylation of lactam 12. The Wacker oxidation of fully substituted pyrrolidine derivative 2,5-trans-17 led to the synthesis of hyacinthacine A(3) (5). Compound 2,5-trans-17 could also serve as a plausible key intermediate for the synthesis of broussonetine sub-class of azasugars. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.085