thioethyl 3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside | 201210-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thioethyl 3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside
• 英文别名: pivaloyl(-2)[Bn(-3)][Bn(-4)]Glc(b)-SEt；[(2S,3R,4S,5R,6R)-2-ethylsulfanyl-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 201210-60-8
• 化学式: C₂₇H₃₆O₆S
• 分子量: 488.645
• InChiKey: HGRVYWNBAPVVPF-RXFVIIJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  thioethyl 3,4-di-O-benzyl-2-pivaloyl-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 32.0h， 生成 3,4-di-O-benzyl-6-O-N-benzylsuccinamyl-2-O-pivaloyl-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-β-D-galactopyranoside
  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 、 sodium methylate 、 二甲基二环氧乙烷 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.75h， 生成 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