(4aR,6S,8R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxaborinine-6,8-diol | 1333965-89-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6S,8R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxaborinine-6,8-diol
• CAS: 1333965-89-1
• 化学式: C₁₂H₁₅BO₅
• 分子量: 250.059
• InChiKey: USWCVOIZJLVWCZ-WYUUTHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-2-脱氧葡萄糖 、 苯硼酸 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 、 、 (4aR,6S,8R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxaborinine-6,8-diol 、 (4aR,6R,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3,2]dioxaborinine-6,8-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.