5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-heptonic acid 1,5-lactam | 197244-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-heptonic acid 1,5-lactam
• 英文别名: (5S,6S)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-hydroxypiperidin-2-one
• CAS: 197244-30-7
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: AHPDQZKFECLYPE-OOZYFLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-heptonic acid 1,5-lactam 在 咪唑 、 4-二甲氨基吡啶 、 sodium periodate 、 sodium hexamethyldisilazane 、 silica gel 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 120.83h， 生成 (E)-(3R,5S,6R)-3-benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-<(2-phenyl)ethen-1-yl>piperidin-2-one
  参考文献：
  名称：

  Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents

  摘要：

  The total synthesis of a potential inhibitor of HIV-protease-the chiral nonracemic six-membered hydroxy lactam 6-has been accomplished, that involves, as key reaction, the highly diastereoselective vinylogous Mannich addition of furan-based silyloxy diene 7 to glyceraldeyde imine 8. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00051-8
• 作为产物：
  描述：

  (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 在 palladium on activated charcoal 叔丁基二甲硅基三氟甲磺酸酯 、 氢气 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 5-amino-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-heptonic acid 1,5-lactam
  参考文献：
  名称：

  Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents

  摘要：

  The total synthesis of a potential inhibitor of HIV-protease-the chiral nonracemic six-membered hydroxy lactam 6-has been accomplished, that involves, as key reaction, the highly diastereoselective vinylogous Mannich addition of furan-based silyloxy diene 7 to glyceraldeyde imine 8. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00051-8

文献信息

• Total synthesis of both enentiomers of trans-β-hydroxyppecolic acid
  作者：Lucia Battistini、Franca Zanardi、Gloria Rassu、Pietro Spanu、Giorgio Pelosi、Giovanna Gasparri Fava、Marisa Belicchi Ferrari、Giovanni Casiraghi

  DOI：10.1016/s0957-4166(97)00344-3

  日期：1997.9

  trans-beta-Hydroxypipecolic acids of both L-and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acids. (C) 1997 Elsevier Science Ltd.
• Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents
  作者：Lucia Battistini、Gloria Rassu、Luigi Pinna、Franca Zanardi、Giovanni Casiraghi

  DOI：10.1016/s0957-4166(99)00051-8

  日期：1999.2

  The total synthesis of a potential inhibitor of HIV-protease-the chiral nonracemic six-membered hydroxy lactam 6-has been accomplished, that involves, as key reaction, the highly diastereoselective vinylogous Mannich addition of furan-based silyloxy diene 7 to glyceraldeyde imine 8. (C) 1999 Elsevier Science Ltd. All rights reserved.