Bz(-2)[Bz(-3)][Bz(-4)][TBDPS(-6)]Glc(b)-SEt | 686723-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bz(-2)[Bz(-3)][Bz(-4)][TBDPS(-6)]Glc(b)-SEt
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-ethylsulfanyloxan-3-yl] benzoate
• CAS: 686723-83-1
• 化学式: C₄₅H₄₆O₈SSi
• 分子量: 775.007
• InChiKey: WOXDTLAEUVMQHD-CGEXMKLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Bz(-2)[Bz(-3)][Bz(-4)][TBDPS(-6)]Glc(b)-SEt 在 N-碘代糖精 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以95%的产率得到2,3,4-tri-O-benzoyl-6-O-[tert-butyl(diphenyl)silyl]-D-glucopyranose
  参考文献：
  名称：

  Mild and Efficient Hydrolysis of Thioglycosides to Glycosyl Hemiacetals Using N-Iodosaccharin

  摘要：

  已开发出一种便捷的方法，利用N-碘代糖精在无需任何共活化剂的条件下对硫苷进行温和水解，生成相应的半缩醛。在反应条件下，大多数用于糖类保护基操作的功能团保持不受影响。

  DOI：

  10.1055/s-2007-977412
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Bz(-2)[Bz(-3)][Bz(-4)][TBDPS(-6)]Glc(b)-SEt
  参考文献：
  名称：

  Catalytic and Chemoselective Glycosylation between “Armed” and “Disarmed” Glycosylp-Trifluoromethylbenzylthio-p-trifluoromethylphenyl Formimidates

  摘要：

  在-78 °C的条件下，使用催化量的TfOH和MS 4A在CH2Cl2中成功实现了新型“有护 arm”和“无护 arm”糖苷p-三氟甲基苯基硫-p-三氟甲基苯基formimidate之间的催化和化学选择性糖苷化。此外，当在-78 °C的tBuOMe或EtCN中进行上述糖苷化反应时，观察到高度的1,2-cis或1,2-trans立体选择性合成。

  DOI：

  10.1246/cl.2002.746

文献信息

• Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions
  作者：Abhishek Santra、Goutam Guchhait、Anup Kumar Misra

  DOI：10.1039/c1gc15122c

  日期：——

  fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。
• Fast oxidation of thioglycosides to glycosyl sulfones using KMnO4/CuSO4·5H2O under neutral reaction conditions
  作者：Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.025

  日期：2006.2

  A rapid oxidation of thioglycosides to glycosyl sulfones has been achieved using a combination of KMnO4 and CuSO(4)center dot 5H(2)O in acetonitrile and water. This reaction protocol has many advantages compared to other methods available for this transformation, including compatibility with acid and base labile functional groups used for the protection of carbohydrates, high yields, fast reaction times, and moderate reaction temperatures. The yields obtained were excellent in all cases. (c) 2005 Elsevier Ltd. All rights reserved.
• Fast and selective oxidation of thioglycosides to glycosyl sulfoxides using KF/m-CPBA
  作者：Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2005.09.132

  日期：2005.11

  A very fast and selective oxidation of thioglycosides to glycosyl sulfoxides has been achieved using KF/m-CPBA in CH3CN-H2O. This protocol has many advantages compared to the currently available methodologies for this transformation in terms of selectivity, yield, reaction time, control of temperature, etc. The yields obtained were excellent in all cases. (c) 2005 Elsevier Ltd. All rights reserved.
• Mild and Efficient Hydrolysis of Thioglycosides to Glycosyl Hemiacetals Using <i>N</i>-Iodosaccharin
  作者：Anup Misra、Pintu Mandal

  DOI：10.1055/s-2007-977412

  日期：——

  A convenient methodology has been developed for the mild hydrolysis of thioglycosides to the corresponding hemiacetals using N-iodosaccharin without any requirement of co-activator. Most of the functional groups used for the protecting group ­manipulation of carbohydrates remain unaffected under the reaction conditions.

  已开发出一种便捷的方法，利用N-碘代糖精在无需任何共活化剂的条件下对硫苷进行温和水解，生成相应的半缩醛。在反应条件下，大多数用于糖类保护基操作的功能团保持不受影响。
• Catalytic and Chemoselective Glycosylation between “Armed” and “Disarmed” Glycosyl<i>p</i>-Trifluoromethylbenzylthio-<i>p</i>-trifluoromethylphenyl Formimidates
  作者：Hiroyuki Chiba、Setsuo Funasaka、Koichi Kiyota、Teruaki Mukaiyama

  DOI：10.1246/cl.2002.746

  日期：2002.7

  Catalytic and chemoselective glycosylation between novel “armed” and “disarmed” glycosyl p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidates was effectively performed in the presence of a catalytic amount of TfOH and MS 4A in CH2Cl2 at -78 °C. In addition, it was noted that highly 1,2-cis or 1,2-trans stereoselective synthesis was established when the above glycosylation was carried out at -78 °C in tBuOMe or EtCN, respectively.

  在-78 °C的条件下，使用催化量的TfOH和MS 4A在CH2Cl2中成功实现了新型“有护 arm”和“无护 arm”糖苷p-三氟甲基苯基硫-p-三氟甲基苯基formimidate之间的催化和化学选择性糖苷化。此外，当在-78 °C的tBuOMe或EtCN中进行上述糖苷化反应时，观察到高度的1,2-cis或1,2-trans立体选择性合成。