methyl 6-O-(6'-O-benzoyl-4'-O-benzyl-2',3'-dideoxy-α-D-erythro-hexopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1221720-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(6'-O-benzoyl-4'-O-benzyl-2',3'-dideoxy-α-D-erythro-hexopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: Bn(-4)[Bz(-6)]2,3-deoxy-D-eryHex(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；[(2R,3S,6S)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 1221720-93-9
• 化学式: C₄₈H₅₂O₁₀
• 分子量: 788.935
• InChiKey: JJHSWVUGHHDCNE-SYSBYLEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6-O-benzoyl-4-O-benzyl-2,3-dideoxy-α-D-erythro-hexopyranosyl acetate 在 三氟甲磺酸三甲基硅酯 、 phenyl 4,6-O-di-benzoyl-2,3-dideoxy-1-thio-D-erythro-hexopyranoside 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl 6-O-(6'-O-benzoyl-4'-O-benzyl-2',3'-dideoxy-α-D-erythro-hexopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 、 methyl 6-O-(6'-O-benzoyl-4'-O-benzyl-2',3'-dideoxy-β-D-erythro-hexopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  远程保护基团对2，3-二脱氧糖基供体糖基化反应的解除武装作用

  摘要：

  研究了C-4和/或C-6位置远程保护基团对2,3-二脱氧糖基供体的糖基化反应的解除武装作用。已经发现，各种糖基的条件下，4-或6- ö -Bn 2,3- dideoxyglycosyl捐助者比相应的4,6-二-更反应性ö -BZ 2,3- dideoxyglycosyl供体。基于这些结果，有效和化学选择性糖基化反应使用4,6-二- ö -Bn糖基乙酸酯和4-OH-6- ö -BZ糖基乙酸乙酯实现，产生良好产率的高2,3- dideoxydisaccharide α-立体选择性。

  DOI：

  10.1016/j.tetlet.2011.02.109

文献信息

• Effective and chemoselective glycosylations using 2,3-unsaturated sugars
  作者：Shunichi Kusumi、Kaname Sasaki、Sainan Wang、Tatsuya Watanabe、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c004204h

  日期：——

  Glycosyl donors containing a double bond between C2 and C3 were designed by mimicking the reaction mechanism of lysozyme-initiated hydrolysis of mucopolysaccharides. It was found that, under various glycosylation conditions, the reactivities of 2,3-unsaturated glycosyl acetates were significantly higher, while those of the corresponding 2,3-unsaturated-4-keto glycosyl acetates were much lower than

  糖基通过模拟溶菌酶引发的粘多糖水解的反应机理，设计了在C2和C3之间含有双键的供体。结果发现，在各种糖基化条件下，2,3-不饱和乙酸糖基乙酸酯的反应性显着较高，而相应的2,3-不饱和-4-酮糖基乙酸酯的反应性则大大低于相应的2,3-不饱和-4-酮糖基乙酸酯。2,3-二脱氧（2，3-饱和的）乙酸糖基酯。基于这些结果，化学选择性糖基化进行了有效地实现通过组合技术中使用三种类型的短步骤糖基供体构建几种类型的脱氧寡糖。此外，发现高反应性的2，3-不饱和乙酸糖基酯可用于合成低反应性叔醇的O-糖苷。
• Chemoselective glycosylations using 2,3-unsaturated-4-keto glycosyl donors
  作者：Shunichi Kusumi、Sainan Wang、Tatsuya Watanabe、Kaname Sasaki、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/b925587g

  日期：——

  2,3-Unsaturated-4-keto glycosyl acetates were found to exhibit low reactivity under several glycosylation conditions. Chemoselective glycosylations were effectively performed using 2,3-unsaturated glycosyl and 2,3-dideoxy glycosyl acetates as armed glycosyl donors, and 2,3-unsaturated-4-keto glycosyl acetates as disarmed glycosyl donors.

  发现2，3-不饱和-4-酮糖基乙酸酯在几种糖基化条件下表现出低反应性。使用2,3-不饱和键可有效地进行化学选择性糖基化糖基 和2,3-二脱氧乙酸糖基酯 糖基 供体和2,3-不饱和-4-酮基乙酸糖基酯被解除武装 糖基 捐助者。
• Armed–disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors
  作者：Satoshi Tomono、Shunichi Kusumi、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1016/j.tetlet.2011.02.109

  日期：2011.5

  The armed–disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective

  研究了C-4和/或C-6位置远程保护基团对2,3-二脱氧糖基供体的糖基化反应的解除武装作用。已经发现，各种糖基的条件下，4-或6- ö -Bn 2,3- dideoxyglycosyl捐助者比相应的4,6-二-更反应性ö -BZ 2,3- dideoxyglycosyl供体。基于这些结果，有效和化学选择性糖基化反应使用4,6-二- ö -Bn糖基乙酸酯和4-OH-6- ö -BZ糖基乙酸乙酯实现，产生良好产率的高2,3- dideoxydisaccharide α-立体选择性。