(1R)-1-[(3aS,5R,6R,6aR)-6-methoxy-2-phenyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3,2]dioxaborol-5-yl]ethane-1,2-diol | 1333966-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R)-1-[(3aS,5R,6R,6aR)-6-methoxy-2-phenyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3,2]dioxaborol-5-yl]ethane-1,2-diol
• CAS: 1333966-01-0
• 化学式: C₁₃H₁₇BO₆
• 分子量: 280.085
• InChiKey: LQKBAGSZFXZOPZ-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-O-甲基-D-葡萄糖 、 苯硼酸 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (4aR,6R,7R,8R,8aR)-8-methoxy-2-phenylhexahydropyrano[3,2-d][1,3,2]dioxaborinine-6,7-diol 、 (4aR,6S,7R,8R,8aR)-8-methoxy-2-phenylhexahydropyrano[3,2-d][1,3,2]dioxaborinine-6,7-diol 、 (1R)-1-[(3aS,5R,6R,6aR)-6-methoxy-2-phenyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3,2]dioxaborol-5-yl]ethane-1,2-diol
  参考文献：
  名称：

  Phenylboronic acid esters of the common 2-deoxy-aldoses

  摘要：

  Phenylboronic acid esters are formed by the three common 2-deoxy aldoses: 2-deoxy-D-erythro-pentose ('2-deoxy-D-ribose'), 2-deoxy-D-lyxo-hexose ('2-deoxy-D-galactose'), and 2-deoxy-D-arabino-hexose ('2deoxy-D-glucose'). The major species that was formed from equimolar quantities of boronic acid and the aldose, was the 3,4-monoester of the pentopyranose in a skew-boat conformation, and the 4,6-monoester in the case of the two hexopyranoses. A double molar quantity of boronic acid led, for both 2-deoxyhexoses, to the diester of the open-chain aldehydo isomer as the major product: the 3,5: 4,6-diester for the lyxo-configured deoxy-hexose, and the 3,4:5,6-diester of the arabino-configured isomer. Minor products of all reactions were identified by a combined NMR/DFT methodology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.031

文献信息

• Phenylboronic acid esters of the common 2-deoxy-aldoses
  作者：David Heß、Peter Klüfers

  DOI：10.1016/j.carres.2011.05.031

  日期：2011.9

  Phenylboronic acid esters are formed by the three common 2-deoxy aldoses: 2-deoxy-D-erythro-pentose ('2-deoxy-D-ribose'), 2-deoxy-D-lyxo-hexose ('2-deoxy-D-galactose'), and 2-deoxy-D-arabino-hexose ('2deoxy-D-glucose'). The major species that was formed from equimolar quantities of boronic acid and the aldose, was the 3,4-monoester of the pentopyranose in a skew-boat conformation, and the 4,6-monoester in the case of the two hexopyranoses. A double molar quantity of boronic acid led, for both 2-deoxyhexoses, to the diester of the open-chain aldehydo isomer as the major product: the 3,5: 4,6-diester for the lyxo-configured deoxy-hexose, and the 3,4:5,6-diester of the arabino-configured isomer. Minor products of all reactions were identified by a combined NMR/DFT methodology. (C) 2011 Elsevier Ltd. All rights reserved.