2-(trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside | 185447-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: trimethylsilylethyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside；(2S,3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-(2-trimethylsilylethoxy)oxan-3-ol
• CAS: 185447-01-2
• 化学式: C₃₂H₄₂O₆Si
• 分子量: 550.767
• InChiKey: UEAPEAOYYSQANW-BQCXQQNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-fluoro-tetrahydro-pyran-3-ol 、 2-(trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 6-[4-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-phenoxy]-hexanoic acid 生成
  参考文献：
  名称：

  Ito, Yukishige; Kanie, Osamu; Ogawa, Tomoya, Angewandte Chemie, 1996, vol. 108, # 21, p. 2691 - 2693

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 在 甲醇 、 二氯二茂铪 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Ito, Yukishige; Kanie, Osamu; Ogawa, Tomoya, Angewandte Chemie, 1996, vol. 108, # 21, p. 2691 - 2693

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of 2-Hydroxy-α-mannopyranosides from Glucal Donors
  作者：Ji-Young Kim、Valeria Di Bussolo、David Y. Gin

  DOI：10.1021/ol006941y

  日期：2001.1.1

  [figure: see text] Direct synthetic access to 2-hydroxy-alpha-mannopyranosides from glucal donors is accomplished via a one-pot stereoselective oxidative glycosylation reaction, employing the reagent combination of dibenzothiophene bis(triflate) and dibenzothiophene-5-oxide.

  [图：见正文]使用二苯并噻吩双（三氟甲磺酸酯）和二苯并噻吩-5-氧化物的试剂组合，通过一锅立体选择性氧化糖基化反应完成了从葡萄糖供体直接合成2-羟基-α-甘露聚糖。
• SYNTHESIS OF 2-(TRIMETHYLSILYL)ETHYL α-d-MANNOPYRANOSIDES REVISITED
  作者：Rina Saksena、Jian Zhang、Pavol Kováč

  DOI：10.1081/car-120016846

  日期：——

  Glycosylation of 2-(trimethylsilyl)ethanol with various ethyl 1-thioglycosides, which were activated with N-iodosuccinimide and silver triflate, was studied. The starting thioglycosides, some prepared for the first time, were obtained conventionally from the corresponding alpha-1-acetates. When beta-1-acetates were more readily available, these were converted to the alpha-anomers by anomerization, prior to the glycosylation. Using ethyl 1-thioglycosides as glycosyl donors, especially those bearing a pivaloyl or a nonparticipating group at O-2, the corresponding 2-(trimethylsilyl)ethyl alpha-D-mannopyranosides were obtained in excellent yields.