(1R,2S,5R,6R,7R,7aR)-6,7-dibenzyloxy-5-tert-butyldiphenylsilyloxymethyl-1,2-dihydroxypyrrolizidin-3-one | 861872-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (1R,2S,5R,6R,7R,7aR)-6,7-dibenzyloxy-5-tert-butyldiphenylsilyloxymethyl-1,2-dihydroxypyrrolizidin-3-one
• 英文别名: (1R,2S,5R,6R,7R,8R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,2-dihydroxy-6,7-bis(phenylmethoxy)-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 861872-82-4
• 化学式: C₃₈H₄₃NO₆Si
• 分子量: 637.848
• InChiKey: PVILLOYDBRLEPW-ZEGBPACMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R,6R,7R,7aR)-6,7-dibenzyloxy-5-tert-butyldiphenylsilyloxymethyl-1,2-dihydroxypyrrolizidin-3-one 在 dimethyl sulfide borane 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以91%的产率得到(1R,2R,5R,6R,7R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxypyrrolizidine
  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：

  methyl (2S,3R)-2,3-dihydroxy-3-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propanoate 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (1R,2S,5R,6R,7R,7aR)-6,7-dibenzyloxy-5-tert-butyldiphenylsilyloxymethyl-1,2-dihydroxypyrrolizidin-3-one
  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