methyl 2,3,4-tri-O-benzyl-6-O-triethylsilyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-triethylsilyl-α-D-glucopyranoside
• 英文别名: triethyl-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]silane
• 化学式: C₃₄H₄₆O₆Si
• 分子量: 578.821
• InChiKey: SIVAMJMBYIOLGS-RUOAZZEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-triethylsilyl-α-D-glucopyranoside 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Highly Efficient and Mild Method for Regioselective De-O-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System

  摘要：

  A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co-2(CO)(8)-Et3SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).

  DOI：

  10.1021/ol902717y
• 作为产物：
  描述：

  三乙基溴硅烷 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 360.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-triethylsilyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of α-D-glucopyranosides via 6-silyl-α-D-glucopyranosyl bromides

  摘要：

  DOI：

  10.1016/s0040-4039(01)81005-4

文献信息

• Investigations to mechanism and applications of the glycosylation protocol employing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycoside donors
  作者：Si-Yu Zhou、Hui-Juan Liu、Qing-Ju Zhang、Jin-Xi Liao、De-Yong Liu、Ming-Dong Li、Jian-Song Sun

  DOI：10.1080/07328303.2022.2045021

  日期：2022.3.24

  Abstract Based on the capability of silyl ethers for efficient glycosylation, the new MTEAN glycosylation protocol utilizing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycosides as donors were extended to one-pot synthesis of nucleosides, late-stage modification of bioactive molecules, and stereoselective construction of 1,2-cis-glucosidic linkages using silyl ethers of the acceptors. Moreover, the

  摘要 基于甲硅烷基醚高效糖基化的能力，利用 8-甲基甲苯磺酰氨基乙炔基-1-萘基 (MTEAN) 糖苷作为供体的新 MTEAN 糖基化方案扩展到核苷的一锅合成、生物活性分子的后期修饰和立体选择性使用受体的甲硅烷基醚构建1,2-顺式-糖苷键。此外，通过对照反应和副产物表征系统地研究了反应机理，从而确定了 TfOH 催化的 ynamide 官能团引发的过程，并通过离去基团的离去形式和真实催化剂的鉴定进一步证实了这一点。
• Highly Efficient and Mild Method for Regioselective De-<i>O</i>-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System
  作者：Zhao-Jun Yin、Bo Wang、Yang-Bing Li、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1021/ol902717y

  日期：2010.2.5

  A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co-2(CO)(8)-Et3SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).
• Stereoselective synthesis of α-D-glucopyranosides via 6-silyl-α-D-glucopyranosyl bromides
  作者：C.P. Fei、T.H. Chan

  DOI：10.1016/s0040-4039(01)81005-4

  日期：1987.1