Methyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 116167-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methylsulfanyloxan-3-yl]isoindole-1,3-dione
• CAS: 116167-61-4
• 化学式: C₁₅H₁₇NO₆S
• 分子量: 339.369
• InChiKey: CHWRJXDFODIPGB-LEQHPZHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 三氯化铝 、 二甲胺基甲硼烷 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methylsulfanyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Stereo- and regio-controlled, total synthesis of the Leb antigen, III4 FucIV2FucLcOSe4 Cer

  摘要：

  DOI：

  10.1016/s0008-6215(00)90162-9
• 作为产物：
  描述：

  甲基3,4,6-三-O-乙酰-2-脱氧-2-邻苯二甲酰亚氨基-1-硫代-β-D-吡喃葡萄糖苷 生成 Methyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Stereo- and regio-controlled, total synthesis of the Leb antigen, III4 FucIV2FucLcOSe4 Cer

  摘要：

  DOI：

  10.1016/s0008-6215(00)90162-9

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.
• Hotta, Kenji; Ishida, Hideharu; Kiso, Makoto, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 2, p. 175 - 192
  作者：Hotta, Kenji、Ishida, Hideharu、Kiso, Makoto、Hasegawa, Akira

  DOI：——

  日期：——