(1R,2R,5R,6R,7R,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine | 861872-84-6

• 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: (1R,2R,5R,6R,7R,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine
• 英文别名: (1R,2R,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol；(1R,2R,5R,6R,7R,8R)-5-(hydroxymethyl)-6,7-bis(phenylmethoxy)-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2-diol
• CAS: 861872-84-6
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: DXUUDIDMBICQMP-WHVWYTALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,5R,6R,7R,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以87%的产率得到6,7-diepi-casuarine
  参考文献：
  名称：

  Polyhydroxylated pyrrolizidines. Part 6: A new and concise stereoselective synthesis of (+)-casuarine and its 6,7-diepi isomer, from DMDP

  摘要：

  A new synthesis for (+)-casuarine (1) and its 6,7-diepi isomer (15) in a stereocontrolled manner, is reported herein. All appropriately protected polyhydroxylated pyrrolidine, such as (2R,3R,4R,5R)-3,4-dibenzyloxy-2'-O-tet-t-butyldiphenylsilyl-2,5-bis(hydroxymethl)pyrrolidine (3, protected DMDP), easily available from D-fructose, was chosen as the chiral starting material. Compounds 1 and 15 were obtained from 3, in seven steps, in a 23.2 and 20.5% overall yields, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.004
• 作为产物：
  描述：

  (2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 在 palladium on activated charcoal N-甲基吗啉 、 四氧化锇 、 四丙基高钌酸铵 、 dimethyl sulfide borane 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 O-(4-氯苯甲酰)氢奎宁 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 119.0h， 生成 (1R,2R,5R,6R,7R,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine
  参考文献：
  名称：

  Polyhydroxylated pyrrolizidines. Part 6: A new and concise stereoselective synthesis of (+)-casuarine and its 6,7-diepi isomer, from DMDP

  摘要：

  A new synthesis for (+)-casuarine (1) and its 6,7-diepi isomer (15) in a stereocontrolled manner, is reported herein. All appropriately protected polyhydroxylated pyrrolidine, such as (2R,3R,4R,5R)-3,4-dibenzyloxy-2'-O-tet-t-butyldiphenylsilyl-2,5-bis(hydroxymethl)pyrrolidine (3, protected DMDP), easily available from D-fructose, was chosen as the chiral starting material. Compounds 1 and 15 were obtained from 3, in seven steps, in a 23.2 and 20.5% overall yields, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.004

文献信息

• Total Synthesis of Uniflorine A, Casuarine, Australine, 3-<i>epi</i>-Australine, and 3,7-Di-<i>epi</i>-australine from a Common Precursor
  作者：Thunwadee Ritthiwigrom、Anthony C. Willis、Stephen G. Pyne

  DOI：10.1021/jo902355p

  日期：2010.2.5

  A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.

  描述了一种灵活的方法，可从一种常见的手性2,5-二氢吡咯前体非对映选择性地合成吡咯烷核生物碱单花碱A，木麻黄，奥曲林和3- Epi- australine和非天然差向异构体3,7-di- epi - australine 。