(1S,2R,3R,5R,6R,7R,7aS)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine | 1248586-84-6

• 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: (1S,2R,3R,5R,6R,7R,7aS)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine
• 英文别名: (1R,2R,3R,5R,6R,7S,8S)-5-(hydroxymethyl)-3-methyl-6,7-bis(phenylmethoxy)-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2-diol
• CAS: 1248586-84-6
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: OICFRZISJLKZCQ-AUVMZELWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  (1S,2R,3R,5R,6R,7R,7aS)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以68%的产率得到(1S,2R,3R,5R,6R,7R,7aS)-1,2,6,7-tetrahydroxy-3-hydroxymethyl-5-methylpyrrolizidine
  参考文献：
  名称：

  Synthesis of unnatural pentahydroxylated pyrrolizidines: 5-epi- and 5,7a-di-epi-hyacinthacine C1

  摘要：

  Stereocontrolled synthesis of 5-epi- and 5,7a-di-epi-hyacinthacine C-1 (7 and 8), two potential glycosidase inhibitors are described using alpha,beta-unsaturated ketone 9 as homochiral starting material. The key step in the synthesis is the highly diastereoselective dihydroxylation reaction of 9, that allows the obtention of a single bis-hydroxylated ketone (10). Further derivatization into two epimeric mesylate esters followed by internal cyclization form the pyrrolizidinic compounds 7 and 8. This type of compounds can be useful in glycobiology due to their ability to inhibit carbohydrate-processing enzymes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.019
• 作为产物：
  描述：

  (2R,3S,4R,5R)-2-[(1'R,2'S,3'S)-1',2'-diacetyloxy-3'-(methanesulfonyloxy)butyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxypyrrolidine 在 三乙胺 、 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以60%的产率得到(1S,2R,3R,5R,6R,7R,7aS)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine
  参考文献：
  名称：

  Synthesis of unnatural pentahydroxylated pyrrolizidines: 5-epi- and 5,7a-di-epi-hyacinthacine C1

  摘要：

  Stereocontrolled synthesis of 5-epi- and 5,7a-di-epi-hyacinthacine C-1 (7 and 8), two potential glycosidase inhibitors are described using alpha,beta-unsaturated ketone 9 as homochiral starting material. The key step in the synthesis is the highly diastereoselective dihydroxylation reaction of 9, that allows the obtention of a single bis-hydroxylated ketone (10). Further derivatization into two epimeric mesylate esters followed by internal cyclization form the pyrrolizidinic compounds 7 and 8. This type of compounds can be useful in glycobiology due to their ability to inhibit carbohydrate-processing enzymes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.019