methyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-O-picolyl-β-D-glucopyranosyl)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-O-picolyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• 英文别名: 2-[[(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]pyridine
• 化学式: C₆₁H₆₅NO₁₁
• 分子量: 988.187
• InChiKey: NOKLBECZAZAJPT-KGSXZNPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  73
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-(1-ethylthioethylidene)-α-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-O-picolyl-β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  立体选择性糖基化和化学选择性寡糖合成的武装参与小组的发展。

  摘要：

  DOI：

  10.1002/anie.200502694

文献信息

• Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH4
  作者：Yang-Fan Guo、Tao Luo、Guang-Jing Feng、Chun-Yang Liu、Hai Dong

  DOI：10.3390/molecules27185980

  日期：——

  An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH4 and aryl disulfides. This method has been further used in a one-pot reaction to synthesize glycosyl donors having both

  开发了一种从相应的过保护糖苷开始有效合成 2-OH 硫代芳基糖苷的改进方法，其中 1,2-脱水糖是通过糖醛与过氧化氢进行氧化，然后与粗结晶 1,2-脱水糖反应制备的。与 NaBH 4和芳基二硫化物。该方法已进一步用于一锅反应，以合成具有“武装”和“NGP（邻接组参与）”效应的糖基供体。
• How the Arming Participating Moieties can Broaden the Scope of Chemoselective Oligosaccharide Synthesis by Allowing the Inverse Armed−Disarmed Approach
  作者：James T. Smoot、Alexei V. Demchenko

  DOI：10.1021/jo801551r

  日期：2008.11.21

  A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety, a novel neighboring group that is capable of efficient participation via a six-membered intermediate. The application of the picolyl concept to glycosidations of thioimidoyl, thioglycosyl, and trichloroacetimidoyl glycosyl donors is demonstrated. The picolyl moiety also retains the glycosyl donor in the armed state, as opposed to conventional acyl participating moieties. We name this new approach the "inverse armed-disarmed" strategy, because it allows for the chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages. In the context of the oligosaccharide synthesis, the strategy provides trans-trans and trans-cis patterned oligosaccharides as opposed to classic Fraser-Reid's armed-disarmed approach leading to cis-trans and cis-cis linkages.
• Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis
  作者：James T. Smoot、Papapida Pornsuriyasak、Alexei V. Demchenko

  DOI：10.1002/anie.200502694

  日期：2005.11.4