(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-(phenylthio)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran | 113410-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-(phenylthio)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran
• CAS: 113410-03-0
• 化学式: C₆₁H₆₄O₁₀S
• 分子量: 989.239
• InChiKey: DUSXELKIJGJNOC-CZPKAMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  72.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-(phenylthio)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran 、 溶剂黄146 在 palladium on activated charcoal 、 镍 氢气 作用下， 生成 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-((2R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Sulfenate esters as glycosyl acceptors: A novel approach to the synthesis of 2-deoxyglycosides

  摘要：

  DOI：

  10.1016/s0040-4039(00)96191-4
• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 三氟甲磺酸三甲基硅酯 4 A molecular sieve 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-(phenylthio)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6-methoxytetrahydro-2H-pyran
  参考文献：
  名称：

  Sulfenate esters as glycosyl acceptors: A novel approach to the synthesis of 2-deoxyglycosides

  摘要：

  DOI：

  10.1016/s0040-4039(00)96191-4

文献信息

• A Convenient Synthesis of 2-Deoxy-β-D-glucopyranosides
  作者：Rainer Preuss、Richard R. Schmidt

  DOI：10.1055/s-1988-27673

  日期：——

  The O-(2-deoxy-2-phenylthio-α-D-glucopyranosyl) trichloroacetimidate α-3 was obtained from 3,4,6-tri-O-benzyl-D-glucal (1) in a two-step procedure. This compound is a powerful glucopyranosyl donor, which with typical alcohol acceptors provided mainly the corresponding 2-phenylthio-substituted 2-deoxy-β-D-glucopyranosides β-5a to β-5d. These were converted by Raney nickel treatment to the desired 2-deoxy-β-D-glucopyranosides 6 in high yields.

  O-(2-脱氧-2-苯硫基-α-D-吡喃葡萄糖基)三氯乙酰亚胺酯α-3 是通过两步从 3,4,6-三-O-苄基-D-葡萄糖 (1) 获得的程序。该化合物是一种强大的吡喃葡萄糖基供体，它与典型的醇受体主要提供相应的2-苯硫基取代的2-脱氧-β-D-吡喃葡萄糖苷β-5a 至β-5d。这些通过雷尼镍处理以高产率转化为所需的2-脱氧-β-D-吡喃葡萄糖苷6。