1,2:5,6-di-O-isopropylidene-3-O-methylene-[5-(3-tert-butyl-2-hydroxy-benzaldehyde)]-α-D-glucofuranose | 918163-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-O-methylene-[5-(3-tert-butyl-2-hydroxy-benzaldehyde)]-α-D-glucofuranose
• 英文别名: 3-tert-Butyl-5-{[5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]methyl}-2-hydroxybenzaldehyde；5-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]-3-tert-butyl-2-hydroxybenzaldehyde
• CAS: 918163-69-6
• 化学式: C₂₄H₃₄O₈
• 分子量: 450.529
• InChiKey: LYZTWEYKLRCIMQ-QNDFHXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-methylene-[5-(3-tert-butyl-2-hydroxy-benzaldehyde)]-α-D-glucofuranose 、 1,2-二氨基环己烷 以 乙醇 为溶剂， 反应 2.0h， 以53%的产率得到
  参考文献：
  名称：

  Enantioselective epoxidation of non-functionalized alkenes using carbohydrate based salen–Mn(III) complexes

  摘要：

  Three new salen ligands with carbohydrate moieties were prepared from a salicylaldehyde derivative obtained by reaction of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose with 3-tert-butyl-5-(chloro-methyl)-2-hydroxybenzaldehyde. These ligands were coordinated with Mn(III) to give three chiral salen-Mn(III) complexes. The complexes were characterized and employed in the asymmetric epoxidation of unfunctionalized alkenes. Catalytic results showed that although there are no chiral groups on the diimine bridge, these complexes had some enantioselectivity, which indicates the carbohydrate moiety has an asymmetric inducing effect in the epoxidation reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.026
• 作为产物：
  描述：

  2-叔丁基苯酚 在 盐酸 、 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.0h， 生成 1,2:5,6-di-O-isopropylidene-3-O-methylene-[5-(3-tert-butyl-2-hydroxy-benzaldehyde)]-α-D-glucofuranose
  参考文献：
  名称：

  Enantioselective epoxidation of non-functionalized alkenes using carbohydrate based salen–Mn(III) complexes

  摘要：

  Three new salen ligands with carbohydrate moieties were prepared from a salicylaldehyde derivative obtained by reaction of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose with 3-tert-butyl-5-(chloro-methyl)-2-hydroxybenzaldehyde. These ligands were coordinated with Mn(III) to give three chiral salen-Mn(III) complexes. The complexes were characterized and employed in the asymmetric epoxidation of unfunctionalized alkenes. Catalytic results showed that although there are no chiral groups on the diimine bridge, these complexes had some enantioselectivity, which indicates the carbohydrate moiety has an asymmetric inducing effect in the epoxidation reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.026

文献信息

• Oxidative kinetic resolution of 1-phenylethanol catalyzed by sugar-based salen–Mn(III) complexes
  作者：Furong Han、Jiquan Zhao、Yuecheng Zhang、Weiyu Wang、Yanyan Zuo、Junwei An

  DOI：10.1016/j.carres.2008.04.022

  日期：2008.7

  structures were characterized by FTIR, MS, and elemental analysis. The complexes together with two previously reported ones were successfully used as chiral catalysts for the oxidative kinetic resolution (OKR) of 1-phenylethanol using PhI(OAc)2 as an oxidant and KBr as an additive. Excellent enantiomeric excess (up to 89%) of the product was achieved in 0.5h at 20 degrees C. The results showed that the

  合成了三个新的手性Salen-Mn（III）配合物，在Salen配体的水杨醛部分的C-5（5'）位置带有糖。通过FTIR，MS和元素分析对它们的结构进行了表征。配合物与两种先前报道的配合物一起成功地用作手性催化剂，以PhI（OAc）2为氧化剂，KBr为添加剂，用于1-苯基乙醇的氧化动力学拆分（OKR）。在20摄氏度下0.5h内，产物的优异对映体过量（高达89％）。结果表明，配体中水杨醛部分C-5（5'）处的糖对苯甲酸的催化性能有影响。复合体。