isopropyl 6-deoxy-6-N,N-dibenzylamino-1,2:3,4-di-O-isopropylidene-7-C-methyl-D-threo-α-D-galacto-1,5-octopyranuronate | 1338819-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: isopropyl 6-deoxy-6-N,N-dibenzylamino-1,2:3,4-di-O-isopropylidene-7-C-methyl-D-threo-α-D-galacto-1,5-octopyranuronate
• CAS: 1338819-29-6
• 化学式: C₃₂H₄₃NO₈
• 分子量: 569.695
• InChiKey: MCNHUGJQUJBBAC-PIDWQBHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  isopropyl 6-deoxy-6-N,N-dibenzylamino-1,2:3,4-di-O-isopropylidene-7-C-methyl-D-threo-α-D-galacto-1,5-octopyranuronate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 20.0 ℃ 、1.9 MPa 条件下， 反应 104.0h， 生成 6-amino-6,8-dideoxy-1,2:3,4-di-O-isopropylidene-7-C-methyl-L-glycero-α-D-galacto-1,5-octopyranose
  参考文献：
  名称：

  Efficient Synthesis of Direct Precursors of the Carbohydrate Moiety of New Antibacterials 6-Epi-VIC-105555 and 6-Epi-VIC-II

  摘要：

  In search for new antibiotics we have developed a novel route leading to direct precursors of the carbohydrate moieties of new promising antibacterial agents 6-epi-VIC-105555 and 6-epi-VIC-II. The presented synthetic strategy consists of using as starting material the readily available beta-dibenzylamino-alpha-ketoester and application of a sequence of chemical transformations on C-7: olefination or methylation, reduction, deoxygenation of the terminal alcohol, and finally hydrogenation. The desired molecules were obtained in a stereoselective fashion and with good overall yields.

  DOI：

  10.1080/07328303.2011.614982
• 作为产物：
  描述：

  isopropyl 6-desoxy-6-N,N-dibenzylamino-1,2:3,4-di-O-isopropylidene-7-ulo-L-glycero-α-D-galacto-1,5-octopyranuronate 、 甲基锂 在 盐酸 、 水 作用下， 以 乙醚 为溶剂， 以65%的产率得到isopropyl 6-deoxy-6-N,N-dibenzylamino-1,2:3,4-di-O-isopropylidene-7-C-methyl-D-threo-α-D-galacto-1,5-octopyranuronate
  参考文献：
  名称：

  Efficient Synthesis of Direct Precursors of the Carbohydrate Moiety of New Antibacterials 6-Epi-VIC-105555 and 6-Epi-VIC-II

  摘要：

  In search for new antibiotics we have developed a novel route leading to direct precursors of the carbohydrate moieties of new promising antibacterial agents 6-epi-VIC-105555 and 6-epi-VIC-II. The presented synthetic strategy consists of using as starting material the readily available beta-dibenzylamino-alpha-ketoester and application of a sequence of chemical transformations on C-7: olefination or methylation, reduction, deoxygenation of the terminal alcohol, and finally hydrogenation. The desired molecules were obtained in a stereoselective fashion and with good overall yields.

  DOI：

  10.1080/07328303.2011.614982