(2R,3S,4R,5R)-2-[(1'R,2'S,3'S)-1',2'-diacetyloxy-3'-(methanesulfonyloxy)butyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxypyrrolidine | 1248586-82-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S,4R,5R)-2-[(1'R,2'S,3'S)-1',2'-diacetyloxy-3'-(methanesulfonyloxy)butyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxypyrrolidine
• 英文别名: [(2R,3R,4S,5R)-5-[(1R,2S,3S)-1,2-diacetyloxy-3-methylsulfonyloxybutyl]-3,4-bis(phenylmethoxy)pyrrolidin-2-yl]methyl benzoate
• CAS: 1248586-82-4
• 化学式: C₃₅H₄₁NO₁₁S
• 分子量: 683.777
• InChiKey: ZEVRLWIKNDYPFJ-RUHLICMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  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
• 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-dibenzyloxy-N-tert-butyloxycarbonylpyrrolidine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到(2R,3S,4R,5R)-2-[(1'R,2'S,3'S)-1',2'-diacetyloxy-3'-(methanesulfonyloxy)butyl]-5-(benzoyloxymethyl)-3,4-dibenzyloxypyrrolidine
  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