(2R,3R,4S,5R,6R)-2-(2-trimethylsilylethoxy)-6-(trityloxymethyl)oxane-3,4,5-triol | 1173893-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-(2-trimethylsilylethoxy)-6-(trityloxymethyl)oxane-3,4,5-triol
• CAS: 1173893-87-2
• 化学式: C₃₀H₃₈O₆Si
• 分子量: 522.714
• InChiKey: ORZAEWPICJKDNE-JYJZCUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(2-trimethylsilylethoxy)-6-(trityloxymethyl)oxane-3,4,5-triol 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 反应 0.5h， 生成 2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside
  参考文献：
  名称：

  Application of Ball Milling Technology to Carbohydrate Reactions: I. Regioselective Primary Hydroxyl Protection of Hexosides and Nucleoside by Planetary Ball Milling‡

  摘要：

  Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.

  DOI：

  10.1080/07328300802218713
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 、 三苯基氯甲烷 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到(2R,3R,4S,5R,6R)-2-(2-trimethylsilylethoxy)-6-(trityloxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  碳水化合物反应的新选择性，IV：DABCO 介导的碳水化合物的区域选择性初级羟基保护

  摘要：

  摘要 已开发出一种在二氯甲烷中 1,4-二氮杂双环 [2.2.2] 辛烷 (DABCO) 存在下使用三苯甲基氯对醛己糖苷和核苷的伯羟基进行区域选择性三苯甲基化的有效方法。在同一个锅中三苯甲基化产物的后续乙酰化已经成为可能，从而为完全保护的碳水化合物衍生物提供了一种有效的途径，可以化学选择性地加以区分。

  DOI：

  10.1080/00397910802656067

文献信息

• Novel Selectivity in Carbohydrate Reactions, IV: DABCO-Mediated Regioselective Primary Hydroxyl Protection of Carbohydrates
  作者：Bharat Kacheshwar Gadakh、Premanand Ramrao Patil、Satish Malik、K. P. Ravindranathan Kartha

  DOI：10.1080/00397910802656067

  日期：2009.6.9

  Abstract An efficient procedure for the regioselective tritylation of primary hydroxyl group of aldohexopyranosides and nucleosides using trityl chloride in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in dichloromethane has been developed. Subsequent acetylation of the tritylated products in the same pot has been made possible, thereby providing an efficient route to the fully protected carbohydrate

  摘要 已开发出一种在二氯甲烷中 1,4-二氮杂双环 [2.2.2] 辛烷 (DABCO) 存在下使用三苯甲基氯对醛己糖苷和核苷的伯羟基进行区域选择性三苯甲基化的有效方法。在同一个锅中三苯甲基化产物的后续乙酰化已经成为可能，从而为完全保护的碳水化合物衍生物提供了一种有效的途径，可以化学选择性地加以区分。
• Application of Ball Milling Technology to Carbohydrate Reactions: I. Regioselective Primary Hydroxyl Protection of Hexosides and Nucleoside by Planetary Ball Milling‡
  作者：Premanand Ramrao Patil、K. P. Ravindranathan Kartha

  DOI：10.1080/07328300802218713

  日期：2008.7

  Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.