2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-thio)benzimidazole | 1246768-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-thio)benzimidazole
• 英文别名: benzimidazol-2-yl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-6-(1H-benzimidazol-2-ylsulfanyl)-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1246768-82-0
• 化学式: C₄₁H₃₂N₂O₉S
• 分子量: 728.779
• InChiKey: GASADAHRAFUJEE-VWJQFIRJSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  882.1±75.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-thio)benzimidazole 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.75h， 以94%的产率得到methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  S-苯并咪唑基糖苷作为活性-潜在策略合成寡糖的平台

  摘要：

  开展业务：S-苯并咪唑基 (SBiz) 异头部分是一种新的离去基团，可以在多种条件下被激活进行糖基化，包括金属辅助和烷基化途径。应用取代的 SBiz 部分（X=苯甲酰基，见图）可实现活性-潜在和武装-解除武装类型的寡糖组装。

  DOI：

  10.1002/anie.201007212
• 作为产物：
  描述：

  (N-anisoyl)benzimidazol-2-yl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-thio)benzimidazole
  参考文献：
  名称：

  S-苯并咪唑基糖苷作为活性-潜在策略合成寡糖的平台

  摘要：

  开展业务：S-苯并咪唑基 (SBiz) 异头部分是一种新的离去基团，可以在多种条件下被激活进行糖基化，包括金属辅助和烷基化途径。应用取代的 SBiz 部分（X=苯甲酰基，见图）可实现活性-潜在和武装-解除武装类型的寡糖组装。

  DOI：

  10.1002/anie.201007212

文献信息

• <i>S</i>-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active–Latent, Armed–Disarmed, Selective, and Orthogonal Activations
  作者：Scott J. Hasty、Mithila D. Bandara、Nigam P. Rath、Alexei V. Demchenko

  DOI：10.1021/acs.joc.6b02478

  日期：2017.2.17

  (SBiz) imidates as versatile building blocks for oligosaccharide synthesis. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations. This article expands upon the utility of these compounds. The application to practically all common concepts for the expeditious oligosaccharide synthesis including selective, chemoselective, and orthogonal strategies is demonstrated

  本文介绍了S-苯并咪唑基（SBiz）酰亚胺作为寡糖合成的通用组成部分的开发。SBiz酰亚胺最初是作为活性潜伏糖基化的新平台开发的。本文扩展了这些化合物的用途。证明了对低聚糖合成的几乎所有通用概念的应用，包括选择性，化学选择性和正交策略。由于我们加深了对反应机理和SBiz酰亚胺化与各种糖基化启动子相互作用的方式的了解，因此制定了策略成为可能。
• A Comparative Study of Glycosyl Thioimidates as Building Blocks for Chemical Glycosylation
  作者：Sneha C. Ranade、Scott J. Hasty、Alexei V. Demchenko

  DOI：10.1080/07328303.2013.826670

  日期：2013.7.24

  Our results indicate that the reactivity and the activation profile of thioimidate glycosyl donors vary significantly depending on the endocyclic heteroatom (N,O,S). Reactivity diminishes in accordance with the following sequence: O > S > N; and this trend stands for a majority of promoters tested. Acyclic glycosyl thioimidates were found to be generally less reactive than the respective cyclic counterparts. The difference in the reactivity was confirmed in direct competition experiments. These findings made possible a two-step one-pot selective activation using thioimidates as the anomeric leaving group of the glycosyl donor and temporary masking group of the glycosyl acceptor. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the supplemental file.
• Revisit to the Reaction of<i>O</i>-Phenylene Diamine with Thiosemicarbazide to Give Benzimidazole-2-Thione Rather than Benzotriazine-2-Thione and its Glycosylation
  作者：El Sayed H. El Ashry、Aly A. Aly、Mohamed R. Aouad、Mohammed R. Amer

  DOI：10.1080/15257770.2010.501777

  日期：2010.8.13

  Reaction of o-phenylene diamine with thiosemicarbazide did not give benzotriazine-2-thione 2 as reported, although the product was found to be benzimidazole-2-thione 3. Glycosylation of 3 with acetobromo sugars 4a-4b gave the respective thioglycosides 7a-7d in addition to minor products of the nucleosides 8a and 8b, in the case of the gluco- and galacto-analogs, respectively. The regioselectivity of glycosylation reaction has been investigated.