p-methylphenyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 220645-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: p-methylphenyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-(4-methylphenyl)sulfanyl-3-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 220645-07-8
• 化学式: C₆₈H₆₄O₁₃S
• 分子量: 1121.31
• InChiKey: HNCOEDGGHRZCNR-TYZCACJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  82
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  14

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 、 p-methylphenyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 1-(p-tolylthio)azepan-2-one 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 以65%的产率得到methyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf

  摘要：

  N-(p-Methylphenylthio)-epsilon-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.024
• 作为产物：
  描述：

  p=methylphenyl 2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 、 p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 在 silver trifluoromethanesulfonate 、 溴化二甲基溴化锍 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到p-methylphenyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  溴化溴二甲基s银-三氟甲磺酸盐：一种新型强大的促进剂，用于硫代糖苷的活化

  摘要：

  溴化二甲基溴化溴化铵（BDMS）与三氟甲磺酸银结合提供了一种非常有效的亲硫性助催化剂体系，能够激活“解除武装的”和“武装化的”硫代糖苷以形成糖苷键。成功的基于反应性的一锅寡糖装配说明了这种新启动子的有用性。

  DOI：

  10.1002/adsc.200800190

文献信息

• Bromodimethylsulfonium Bromide-Silver Triflate: A New Powerful Promoter System for the Activation of Thioglycosides
  作者：De-Cai Xiong、Li-He Zhang、Xin-Shan Ye

  DOI：10.1002/adsc.200800190

  日期：2008.8.4

  Bromodimethylsulfonium bromide (BDMS) in combination with silver triflate provides a very efficient thiophilic promoter system, capable of activating both “disarmed” and “armed” thioglycosides for glycosidic bond formation. The usefulness of this new promoter is illustrated by a successful reactivity-based one-pot oligosaccharide assembly.

  溴化二甲基溴化溴化铵（BDMS）与三氟甲磺酸银结合提供了一种非常有效的亲硫性助催化剂体系，能够激活“解除武装的”和“武装化的”硫代糖苷以形成糖苷键。成功的基于反应性的一锅寡糖装配说明了这种新启动子的有用性。
• <i>N</i>-(Phenylthio)-ε-caprolactam:  A New Promoter for the Activation of Thioglycosides
  作者：Sergio G. Durón、Tülay Polat、Chi-Huey Wong

  DOI：10.1021/ol0400084

  日期：2004.3.1

  N-(Phenylthio)-epsilon-caprolactam (1) has been applied as a new promoter for the activation of thioglycosides. This proceeds by the reaction of 1 with trifluoromethansulfonic anhydride, which subsequently activates the thioglycoside for glycosidic bond formation. Notably, the reaction proceeds efficiently at room temperature and is adaptable to our reactivity-based one-pot oligosaccharide synthesis.
• Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf
  作者：Sajal Kumar Maity、Nabamita Basu、Rina Ghosh

  DOI：10.1016/j.carres.2012.03.024

  日期：2012.6

  N-(p-Methylphenylthio)-epsilon-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy. (C) 2012 Elsevier Ltd. All rights reserved.