(2R,3S,4R,5R)-2-[(1'R,2'S)-1',2'-diacetyloxy-3'-oxobutyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxy-N-tert-butyloxycarbonylpyrrolidine | 1248586-79-9

• 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,3S,4R,5R)-2-[(1'R,2'S)-1',2'-diacetyloxy-3'-oxobutyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxy-N-tert-butyloxycarbonylpyrrolidine
• CAS: 1248586-79-9
• 化学式: C₃₉H₄₅NO₁₁
• 分子量: 703.786
• InChiKey: OVYKJOMRQMUONP-GFPTWPQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  143.97
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-2-[(1'R,2'S)-1',2'-diacetyloxy-3'-oxobutyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxy-N-tert-butyloxycarbonylpyrrolidine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以25%的产率得到(2R,3S,4R,5R)-2-[(1'R,2'R,3'S)-1',2'-diacetyloxy-3'-hydroxybutyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxy-N-tert-butyloxycarbonylpyrrolidine
  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：

  (2S,3S,4R,5R)-2-[(1'R,2'S)-1',2'-dihydroxy-3'-oxobutyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxy-N-tert-butyloxycarbonylpyrrolidine 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 以86%的产率得到(2R,3S,4R,5R)-2-[(1'R,2'S)-1',2'-diacetyloxy-3'-oxobutyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxy-N-tert-butyloxycarbonylpyrrolidine
  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