thioethyl 6-O-acetyl-3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside | 288630-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thioethyl 6-O-acetyl-3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside
• 英文别名: pivaloyl(-2)[Bn(-3)][Bn(-4)]Glc6Ac(b)-SEt；[(2S,3R,4S,5R,6R)-6-(acetyloxymethyl)-2-ethylsulfanyl-4,5-bis(phenylmethoxy)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 288630-55-7
• 化学式: C₂₉H₃₈O₇S
• 分子量: 530.683
• InChiKey: QIUJVVQLRKJXHH-SEFGFODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  thioethyl 6-O-acetyl-3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以100%的产率得到thioethyl 3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Linker Influence on the Stereochemical Outcome of Glycosylations Utilizing Solid Support-Bound Glycosyl Phosphates

  摘要：

  [GRAPHICS]Glycosyl phosphates can be readily accessed on a solid support via a three-step procedure from support-bound glycals. These resin-bound glycosyl phosphates were successfully used as glycosylating agents for coupling with a series of nucleophiles. The stereochemical outcome of disaccharide formation was dependent on the nature of the linker connecting the saccharide to the polymer. Interestingly, other glycosyl donors such as thioglycosides and trichloroacetimidates did not exhibit such a dependence, indicating a different reaction mechanism for glycosylation.

  DOI：

  10.1021/ol026276o
• 作为产物：
  描述：

  6-O-acetyl-3,4-di-O-benzyl-D-glucal 在 4-二甲氨基吡啶 、 二甲基二环氧乙烷 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 7.25h， 生成 thioethyl 6-O-acetyl-3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Linker Influence on the Stereochemical Outcome of Glycosylations Utilizing Solid Support-Bound Glycosyl Phosphates

  摘要：

  [GRAPHICS]Glycosyl phosphates can be readily accessed on a solid support via a three-step procedure from support-bound glycals. These resin-bound glycosyl phosphates were successfully used as glycosylating agents for coupling with a series of nucleophiles. The stereochemical outcome of disaccharide formation was dependent on the nature of the linker connecting the saccharide to the polymer. Interestingly, other glycosyl donors such as thioglycosides and trichloroacetimidates did not exhibit such a dependence, indicating a different reaction mechanism for glycosylation.

  DOI：

  10.1021/ol026276o

文献信息

• A novel 4,5-dibromooctane-1,8-diol linker for solid-phase oligosaccharide synthesis
  作者：Luis G Melean、Wilm-Christian Haase、Peter H Seeberger

  DOI：10.1016/s0040-4039(00)00663-8

  日期：2000.6

  A novel 4,5-dibromooctane-1,8-diol linker was applied to the solid support preparation of a β-(1→6) trisaccharide employing electrophilic activation of thioethyl glycoside building blocks. Debromination of the resin-bound linker-double bond could effectively be carried out by elimination, followed by olefin cross-metathesis revealing the desired trimeric n-pentenyl glycoside. High-resolution Magic

  新型的4,5-二溴辛烷-1,8-二醇连接基通过硫代乙基糖苷结构单元的亲电活化作用，被用于β-（1→6）三糖的固相载体制备。可以通过消除有效地进行树脂结合的连接子-双键的脱溴，然后进行烯烃交叉复分解，从而揭示所需的三聚正戊烯基糖苷。高分辨率魔角旋转核磁共振光谱法用作监测和发展固相反应的分析工具。