4-O-benzyl-1-deoxy-2,3-O-isopropylidene-L-lyxo-5-hexenitol | 1138337-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-benzyl-1-deoxy-2,3-O-isopropylidene-L-lyxo-5-hexenitol
• 英文别名: (2S,3R,4R)-2,3-O-isopropylidene-hex-5-ene-2,3,4-triol；(1S)-1-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS: 1138337-92-4
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: GPJHYNOTVRBZAZ-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  C₉H₁₄O₃ 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-O-benzyl-1-deoxy-2,3-O-isopropylidene-L-xylo-5-hexenitol 、 4-O-benzyl-1-deoxy-2,3-O-isopropylidene-L-lyxo-5-hexenitol
  参考文献：
  名称：

  Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols

  摘要：

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.074

文献信息

• Total Synthesis of (+)-Varitriol
  作者：Miroslav Palík、Ol'ga Karlubíková、Angelika Lásiková、Jozef Kožíšek、Tibor Gracza

  DOI：10.1002/ejoc.200801070

  日期：2009.2

  The total synthesis of natural (+)-varitriol (1) was accomplished by starting from dimethyl L-tartrate. The keyfeatures were a substrate selective and diastereoselective PdII-catalysed bicyclisation of unsaturated protected triol 9 followed by regioselective ring-opening of bicyclic skeleton 10. The absolute configuration of the target was confirmed by single-crystal X-ray analysis for the first time

  天然 (+)-varitriol (1) 的全合成是通过从 L-酒石酸二甲酯开始完成的。关键特征是不饱和受保护三醇 9 的底物选择性和非对映选择性 PdII 催化双环化，然后双环骨架 10 的区域选择性开环。目标的绝对构型首次通过单晶 X 射线分析得到证实。 © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols
  作者：Miroslav Palík、Oľga Karlubíková、Daniela Lackovičová、Angelika Lásiková、Tibor Gracza

  DOI：10.1016/j.tet.2010.04.074

  日期：2010.7

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.