BPh(β-D-ery-dPenp3,4H-2) | 53225-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: BPh(β-D-ery-dPenp3,4H-2)
• 英文别名: O³,O⁴-phenylboranediyl-D-erythro-2-deoxy-pentose；O³,O⁴-phenylboranediyl-β-D-erythro-2-deoxy-pentopyranose；I(2)-D-erythro-Pentopyranose, cyclic 3,4-(B-phenylboronate)；(3aR,6R,7aS)-2-phenyl-4,6,7,7a-tetrahydro-3aH-[1,3,2]dioxaborolo[4,5-c]pyran-6-ol
• CAS: 53225-62-0
• 化学式: C₁₁H₁₃BO₄
• 分子量: 220.033
• InChiKey: ISNOLOSSNZHJLO-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  BPh(β-D-ery-dPenp3,4H-2) 、 对甲苯磺酰氯 在 吡啶 作用下， 生成 O³,O⁴-phenylboranediyl-O¹-(toluene-4-sulfonyl)-β-D-erythro-2-deoxy-pentopyranose
  参考文献：
  名称：

  Guseva,A.S. et al., Journal of general chemistry of the USSR, 1974, vol. 44, p. 1145 - 1149

  摘要：

  DOI：
• 作为产物：
  描述：

  2-deoxy-D-ribose 、 苯硼酸 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 BPh(α-D-ery-dPenp3,4H-2) 、 BPh(α-D-ery-dPenp1,3H-2) 、 BPh(β-D-ery-dPenp3,4H-2)
  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

• Guseva,A.S. et al., Journal of general chemistry of the USSR, 1974, vol. 44, p. 1145 - 1149
  作者：Guseva,A.S. et al.

  DOI：——

  日期：——
• 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.