methyl 1,3,4-tri-O-benzyl-β-L-erythro-pent-2-ulofuranoside | 216769-91-4

• 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: methyl 1,3,4-tri-O-benzyl-β-L-erythro-pent-2-ulofuranoside
• 英文别名: methyl 1,3,4-tri-O-benzyl-β-L-erythro-pentulofuranoside
• CAS: 216769-91-4
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: DISMPEQBOAPKJG-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 1,3,4-tri-O-benzyl-β-L-erythro-pent-2-ulofuranoside 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以80%的产率得到1,3,4-tri-O-benzyl-α,β-L-erythro-pent-2-ulofuranose
  参考文献：
  名称：

  Synthesis of Protein Conjugates of 2-Carboxy-L-Arabinitol 5-Phosphate and 2-Carboxy-L-Ribitol 5-Phosphate

  摘要：

  The synthesis of 5-O-[5-(pentanoic acid)]-phosphono-L-erythro-pent-2-ulose 2 was successfully achieved by coupling benzyl 5-hydroxypentanoate 9b and 1-O-benzyl-L-erythro-pent-2-ulose ethane-1,2-diyl dithioacetal 13 with the enediol pyrophosphate 18. Compound 2 was coupled to carrier proteins, porcine thyroglobuline and bovine serum albumin and the conjugates were treated with KCN to give conjugates of the hapten 1, designed to raise catalytic antibodies.

  DOI：

  10.1080/07328309808001895
• 作为产物：
  描述：

  methyl β-L-erythro-pent-2-ulofuranoside 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以58%的产率得到methyl 1,3,4-tri-O-benzyl-β-L-erythro-pent-2-ulofuranoside
  参考文献：
  名称：

  Synthesis of Protein Conjugates of 2-Carboxy-L-Arabinitol 5-Phosphate and 2-Carboxy-L-Ribitol 5-Phosphate

  摘要：

  The synthesis of 5-O-[5-(pentanoic acid)]-phosphono-L-erythro-pent-2-ulose 2 was successfully achieved by coupling benzyl 5-hydroxypentanoate 9b and 1-O-benzyl-L-erythro-pent-2-ulose ethane-1,2-diyl dithioacetal 13 with the enediol pyrophosphate 18. Compound 2 was coupled to carrier proteins, porcine thyroglobuline and bovine serum albumin and the conjugates were treated with KCN to give conjugates of the hapten 1, designed to raise catalytic antibodies.

  DOI：

  10.1080/07328309808001895

文献信息

• An expedient synthesis of l-ribulose and derivatives
  作者：Geeta Meher、Ramanarayanan Krishnamurthy

  DOI：10.1016/j.carres.2011.01.013

  日期：2011.5

  A significant improvement in the production of L-ribulose from inexpensive and commercially available starting materials, L-arabinose and sodium aluminate, is demonstrated. This has facilitated expeditious access to gram-scale quantities of L-ribulofuranoside derivatives. (C) 2011 Elsevier Ltd. All rights reserved.