phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside | 1384861-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• CAS: 1384861-27-1
• 化学式: C₆₇H₆₂O₁₃S
• 分子量: 1107.29
• InChiKey: XPTFNMBJTJPZNQ-BXWRTAMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.89
• 重原子数：
  81.0
• 可旋转键数：
  24.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  143.51
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  phenyl 2,3,4-tri-O-benzoyl-β-D-thioglucopyranoside 、 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 作用下， 生成 phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 、 phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly

  摘要：

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.

  DOI：

  10.1021/jo201117s

文献信息

• Visible-light-induced photoacid catalysis: application in glycosylation with <i>O</i>-glycosyl trichloroacetimidates
  作者：Gaoyuan Zhao、Juncheng Li、Ting Wang

  DOI：10.1039/d1cc04887b

  日期：——

  The development of visible-light-induced photoacid catalyzed glycosylation is reported.

  可见光诱导的光酸催化糖基化反应的发展被报道。
• 2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis
  作者：Hemali D Premathilake、Alexei V Demchenko

  DOI：10.3762/bjoc.8.66

  日期：——

  The O-allylphenyl (AP) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions, through both direct and remote pathways. Differentiation between the two activation pathways was achieved in a mechanistic study. The orthogonal-type activation of the AP moiety along with common thioglycosides allows for the execution of efficient

  O-烯丙基苯基 (AP) 异头部分被研究为一种新的离去基团，可以在各种条件下通过直接和远程途径激活化学糖基化。在机械研究中实现了两种激活途径之间的区别。AP 部分的正交型激活与常见的硫糖苷一起允许执行有效的寡糖组装。
• Thioperoxide-Mediated Activation of Thioglycoside Donors
  作者：Hongwen He、Xiangming Zhu

  DOI：10.1021/ol501211z

  日期：2014.6.6

  trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a powerful thiophilic promoter system, capable of activating different thioglycosides. Both armed and disarmed thioglycosides were activated effectively in the presence of different glycosyl acceptors, giving glycosidation products in high to excellent yields. A plausible activation pathway was also proposed and supported by isolating side-products

  硫过氧化物（1）与三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）结合提供了强大的亲硫促进剂体系，能够活化不同的硫糖苷。在存在不同的糖基受体的情况下，武装和解除武装的硫代糖苷都被有效地激活，从而以高到极好的收率得到糖苷化产物。还提出了一条可行的活化途径，并通过分离副产物三氟甲基苯基二硫化物（CF 3 SSPh）和烯烃（42）予以支持。