1-((2Z,6Z,10Z,14E,18E,22E)-1-benzyloxy-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-13-yl)sulfonyl-4-methylbenzene | 1186313-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-((2Z,6Z,10Z,14E,18E,22E)-1-benzyloxy-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-13-yl)sulfonyl-4-methylbenzene
• CAS: 1186313-56-3
• 化学式: C₄₉H₇₀O₃S
• 分子量: 739.159
• InChiKey: HDZUXXWYEDEFIC-NFWYETQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.29
• 重原子数：
  53.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-((2Z,6Z,10Z,14E,18E,22E)-1-benzyloxy-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-13-yl)sulfonyl-4-methylbenzene 在 lithium 、 乙胺 、 天然橡胶 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 0.67h， 以74%的产率得到3,7,11,15,19,23,27-heptamethyloctaeicosa-2Z,6Z,10Z,14E,18E,22E,26-heptaen-1-ol
  参考文献：
  名称：

  Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

  摘要：

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.032
• 作为产物：
  描述：

  all-trans-geranylgeranyl toluene-p-sulphonyl sulphone 、 (Z,Z,Z)-12-benzyloxy-1-chloro-2,6,10-trimethyldodeca-2,6,10-triene 在 正丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 3.67h， 以93%的产率得到1-((2Z,6Z,10Z,14E,18E,22E)-1-benzyloxy-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-13-yl)sulfonyl-4-methylbenzene
  参考文献：
  名称：

  Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

  摘要：

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.032