3-O-pivaloyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 67104-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-pivaloyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: [(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] 2,2-dimethylpropanoate
• CAS: 67104-31-8
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: DXOPBIYEJGESSW-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-pivaloyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 溶剂黄146 作用下， 生成 2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives

  摘要：

  In this paper we report the synthesis of twelve 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives and the results obtained on their effects in inducing erythroid differentiation of human leukemic K562 cells. The data obtained demonstrate that two of the newly synthetized compounds are able to induce erythroid differentiation of K562 cells. In addition, these same compounds potentiate K562 erythroid differentiation induced by cytosine arabinoside, retinoic acid and mithramycin. Inducers of erythroid differentiation stimulating fetal gamma-globin synthesis could be considered for possible use in the experimental therapy of hematological diseases associated with a failure in the expression of adult beta-globin genes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00547-8
• 作为产物：
  描述：

  3-O-[(t-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 potassium fluoride 、 N-(methylpolystyrene)-4-(methylamino)pyridine 、 四丁基溴化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 0.28h， 生成 3-O-pivaloyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  RAPID CARBOHYDRATE PROTECTING GROUP MANIPULATIONS ASSISTED BY MICROWAVE DIELECTRIC HEATING

  摘要：

  The protocols for oligosaccharide synthesis are often tedious due to extended synthetic routes and reaction times. We herein describe methods assisted by microwave dielectric heating, which enable very short reaction times and high yields for the introduction and removal of eleven of the most commonly used protecting groups in carbohydrate syntheses. Several examples are reported, where solid supported reagents in combination with microwave dielectric heating have been used. This results in both faster and easier synthesis and purification.

  DOI：

  10.1081/car-100105712

文献信息

• RAPID CARBOHYDRATE PROTECTING GROUP MANIPULATIONS ASSISTED BY MICROWAVE DIELECTRIC HEATING
  作者：Eva Söderberg、Jacob Westman、Stefan Oscarson*

  DOI：10.1081/car-100105712

  日期：2001.6.30

  The protocols for oligosaccharide synthesis are often tedious due to extended synthetic routes and reaction times. We herein describe methods assisted by microwave dielectric heating, which enable very short reaction times and high yields for the introduction and removal of eleven of the most commonly used protecting groups in carbohydrate syntheses. Several examples are reported, where solid supported reagents in combination with microwave dielectric heating have been used. This results in both faster and easier synthesis and purification.
• Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives
  作者：Giorgio Catelani、Fabio Osti、Nicoletta Bianchi、Maria Camilla Bergonzi、Felicia D'Andrea、Roberto Gambari

  DOI：10.1016/s0960-894x(99)00547-8

  日期：1999.11

  In this paper we report the synthesis of twelve 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives and the results obtained on their effects in inducing erythroid differentiation of human leukemic K562 cells. The data obtained demonstrate that two of the newly synthetized compounds are able to induce erythroid differentiation of K562 cells. In addition, these same compounds potentiate K562 erythroid differentiation induced by cytosine arabinoside, retinoic acid and mithramycin. Inducers of erythroid differentiation stimulating fetal gamma-globin synthesis could be considered for possible use in the experimental therapy of hematological diseases associated with a failure in the expression of adult beta-globin genes. (C) 1999 Elsevier Science Ltd. All rights reserved.