methyl 6-amino-7-C-methyl-6,7,8-trideoxy-1-thio-L-glycero-α-D-galacto-1,5-octopyranoside | 1338819-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-amino-7-C-methyl-6,7,8-trideoxy-1-thio-L-glycero-α-D-galacto-1,5-octopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[(1S)-1-amino-2-methylpropyl]-6-methylsulfanyloxane-3,4,5-triol
• CAS: 1338819-39-8
• 化学式: C₁₀H₂₁NO₄S
• 分子量: 251.347
• InChiKey: FYEFLEUMNQBKHG-HQBQHRAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 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 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 palladium 10% on activated carbon 、 氢溴酸 、 氢气 、 silver(I) acetate 、 三乙胺 、 二异丙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、1.9 MPa 条件下， 反应 123.75h， 生成 methyl 6-amino-7-C-methyl-6,7,8-trideoxy-1-thio-L-glycero-α-D-galacto-1,5-octopyranoside
  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

文献信息

• Efficient Synthesis of Direct Precursors of the Carbohydrate Moiety of New Antibacterials 6-Epi-VIC-105555 and 6-Epi-VIC-II
  作者：Tomasz K. Olszewski、Fiona Serra、Claude Grison、Patric Herson

  DOI：10.1080/07328303.2011.614982

  日期：2011.2.1

  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.