(2S,3S,4S,5S,6R)-2-[(2R,3S,4S,5S,6R)-2-((2S,3S,4S,5S,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol | 862476-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5S,6R)-2-[(2R,3S,4S,5S,6R)-2-((2S,3S,4S,5S,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS: 862476-85-5
• 化学式: C₂₁H₃₆O₁₆
• 分子量: 544.507
• InChiKey: KIRFTTWZLYIZTI-FJDGIISLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.36
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  257.68
• 氢给体数：
  10.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5S,6R)-2-[(2R,3S,4S,5S,6R)-2-((2S,3S,4S,5S,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 、 乙酸酐 在 吡啶 作用下， 以34 mg的产率得到allyl 3,4,6-tri-O-acetyl-2-O-[3,4,6-tri-O-acetyl-3-O-{2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl}-α-D-mannopyranosyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Efficient Installation of β-Mannosides Using a Dehydrative Coupling Strategy

  摘要：

  A new coupling procedure for the construction of the challenging beta-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of beta-mannosides in excellent yield. The stereoselectivity is generally good but influenced by the exact nature of the glycosylating agent and the nucleophile.

  DOI：

  10.1021/ol051038p
• 作为产物：
  描述：

  D-甘露糖 在 三氟甲磺酸酐 、 三氟甲磺酸三甲基硅酯 、 二苯基亚砜 、 2,4,5-tri-tert-butylpyrimidine 、 三氟化硼乙醚 、 二正丁基氧化锡 、 对甲苯磺酸 、 1,2-乙二硫醇 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.25h， 生成 (2S,3S,4S,5S,6R)-2-[(2R,3S,4S,5S,6R)-2-((2S,3S,4S,5S,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Efficient Installation of β-Mannosides Using a Dehydrative Coupling Strategy

  摘要：

  A new coupling procedure for the construction of the challenging beta-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of beta-mannosides in excellent yield. The stereoselectivity is generally good but influenced by the exact nature of the glycosylating agent and the nucleophile.

  DOI：

  10.1021/ol051038p