3-[(3-benzyloxycarbonylamino)propylthio]propyl (methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate)-(1→4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside | 1624284-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(3-benzyloxycarbonylamino)propylthio]propyl (methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate)-(1→4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS: 1624284-91-8
• 化学式: C₁₀₄H₁₁₅N₇O₂₄S
• 分子量: 1879.16
• InChiKey: KAIPDBCTOMNADH-TZPBEUIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.74
• 重原子数：
  136.0
• 可旋转键数：
  51.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  354.59
• 氢给体数：
  1.0
• 氢受体数：
  27.0

反应信息

• 作为产物：
  描述：

  benzyl N-(3-mercaptopropyl)carbamate 、 在 三乙基硼 、 邻苯二酚 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到3-[(3-benzyloxycarbonylamino)propylthio]propyl (methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate)-(1→4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Repairing the Thiol-Ene Coupling Reaction

  摘要：

  AbstractThiol‐ene coupling (TEC) reactions emerged as one of the most useful processes for coupling different molecular units under reaction mild conditions. However, TEC reactions involving weak CH bonds (allylic and benzylic fragments) are difficult to run and often low yielding. Mechanistic studies demonstrate that hydrogen‐atom transfer processes at allylic and benzylic positions are responsible for the lack of efficiency of the radical‐chain process. These competing reactions cannot be prevented, but reported herein is a method to repair the chain process by running the reaction in the presence of triethylborane and catechol. Under these reaction conditions, a unique repair mechanism leads to an efficient chain reaction, which is demonstrated with a broad range of anomeric O‐allyl sugar derivatives including mono‐, di‐, and tetrasaccharides bearing various functionalities and protecting groups.

  DOI：

  10.1002/anie.201309984