isopropyl 6-N,N-dibenzylamino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-methylene-L-glycero-α-D-galacto-1,5-octopyranuronate | 1338819-18-3

• 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-N,N-dibenzylamino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-methylene-L-glycero-α-D-galacto-1,5-octopyranuronate
• CAS: 1338819-18-3
• 化学式: C₃₂H₄₁NO₇
• 分子量: 551.68
• InChiKey: NXURJIAEDTWFSO-PLXCMXOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  75.69
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  isopropyl 6-N,N-dibenzylamino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-methylene-L-glycero-α-D-galacto-1,5-octopyranuronate 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢溴酸 、 氢气 、 silver(I) acetate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， -78.0~20.0 ℃ 、1.9 MPa 条件下， 反应 100.75h， 生成 6-trifluoroacetylamino-7-C-methyl-6,7,8-trideoxy-2,3,4-tri-O-acetyl-L-glycero-α-D-galacto-1,5-octopyranosyl chloride
  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 、 甲基三苯基溴化膦 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.0h， 以65%的产率得到isopropyl 6-N,N-dibenzylamino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-methylene-L-glycero-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