2,3,4-tri-O-benzyl-L-arabino-pentodialdose 1,1-di(n-propyl)dithioacetal | 153322-92-0

• 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: 2,3,4-tri-O-benzyl-L-arabino-pentodialdose 1,1-di(n-propyl)dithioacetal
• CAS: 153322-92-0
• 化学式: C₃₂H₄₀O₄S₂
• 分子量: 552.799
• InChiKey: CAVLXDIHAARRDZ-RWSKJCERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.55
• 重原子数：
  38.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-L-arabino-pentodialdose 1,1-di(n-propyl)dithioacetal 在 N-溴代丁二酰亚胺(NBS) 、 无水碳酸镉 、 二甲基硫 、 碳酸氢钠 、 mercury dichloride 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 31.5h， 生成 (3S,3aS,4S,5S,6S)-2-(4-bromophenyl)-3-carboxymethyl-4,5,6-tribenzyloxy-2,3,3a,4,5,6-hexahydro-cyclopentapyrazole
  参考文献：
  名称：

  Cycloaddition reactions of carbohydrate derivatives. Part 8: Intramolecular cycloaddition of nitrilimines derived from sugars

  摘要：

  Nitrilimines containing a carbon-carbon double bond were prepared in several steps from 3,3,4-tri-O-benzyl-D-xylose, D-ribose and L-arabinose derivatives and their intramolecular 1,3-dipolar cycloaddition reactions were studied. The results were examined with molecular modelling and compared with the literature data for similar cycloadditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00050-7
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-galactose 1,1-di(n-propyl)dithioacetal 在 lead(IV) acetate 作用下， 以 甲苯 为溶剂， 生成 2,3,4-tri-O-benzyl-L-arabino-pentodialdose 1,1-di(n-propyl)dithioacetal
  参考文献：
  名称：

  Cycloaddition reactions of carbohydrate derivatives. Part 8: Intramolecular cycloaddition of nitrilimines derived from sugars

  摘要：

  Nitrilimines containing a carbon-carbon double bond were prepared in several steps from 3,3,4-tri-O-benzyl-D-xylose, D-ribose and L-arabinose derivatives and their intramolecular 1,3-dipolar cycloaddition reactions were studied. The results were examined with molecular modelling and compared with the literature data for similar cycloadditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00050-7

文献信息

• Pentodialdose mercaptal derivatives: New chiral C5 synthetic building blocks
  作者：Imre Kovács、Zoltán Tóth、Pál Herczegh、Ferenc Sztaricskai

  DOI：10.1016/s0957-4166(00)80076-2

  日期：1993.10

  Three tribenzyloxy derivatives of the title compounds with D-xylo, L-arabino and D-lyxo configuration were prepared from naturally abundant hexoses in five steps.