6-O-(2,2-dimethylpropanoyl)-1,2-O-isopropylidene-α-D-glucofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(2,2-dimethylpropanoyl)-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: 1,2-O-isopropylidene-6-O-pivaloyl-α-D-glucofuranose；1,2-O-isopropylidene-6-O-(trimethylacetyl)-α-D-glucofuranose；[(2R)-2-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] 2,2-dimethylpropanoate
• 化学式: C₁₄H₂₄O₇
• 分子量: 304.34
• InChiKey: AHUZRSISMIXYPX-RCZSTQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 6-O-(2,2-dimethylpropanoyl)-1,2-O-isopropylidene-α-D-glucofuranose 在 对甲苯磺酸 作用下， 反应 1.0h， 以45.5%的产率得到6-O-pivaloyl-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Glucose transporter 1-mediated vascular translocation of nanomedicines enhances accumulation and efficacy in solid tumors

  摘要：

  Nanomedicine modification with ligands directed to receptors on tumor blood vessels has the potential for selectively enhancing nanomedicine accumulation in malignant tissues by overcoming the vascular barrier of tumors. Nevertheless, the development of broadly applicable ligand approaches capable of promoting the transvascular transport of nanomedicines in a wide spectrum of tumors has been elusive so far. By considering the indispensable and persistent glycolytic fueling of tumors, we developed glucose-installed polymeric micelles loading cisplatin (Gluc-CDDP/m) targeting the glucose transporter 1 (GLUT1), which is overexpressed in most tumors and present on vascular endothelial cells, toward improving the delivery efficiency and therapeutic efficacy. The design of the glucose ligands on Gluc-CDDP/m was engineered to control the conjugation via the carbon 6 of the glucose moieties, as well as the ligand density on the poly (ethylene glycol) (PEG) shell of the micelles. The series of micelles was then studied in vitro and in vivo against GLUT1-high human squamous cell carcinoma of the head and neck OSC-19 cells and GLUT1-low human glioblastoma-astrocytoma U87MG cells. Our results showed that precisely tuning the micelles to have glucose ligands on 25% of their PEG chains increased the efficacy against the tumors by significantly enhancing the tumor accumulation, even in GLUT1-low U87MG tumors. The enhancement of the intratumoral levels of these micelles was hindered by concomitant administration of glucose, or the GLUT1 inhibitor STF-31, confirming a GLUT1/glucose-mediated increment of the accumulation. Intravital confocal laser scanning microscopy imaging of tumor tissues further demonstrated the rapid extravasation and penetration of Gluc-CDDP/m in OSC-19 tumors compared to non-targeted CDDP/m. These findings indicate GLUT1-targeting as a promising approach for overcoming the vascular barrier and boosting the delivery of nanomedicine in tumors.

  DOI：

  10.1016/j.jconrel.2019.02.021
• 作为产物：
  描述：

  (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 在 palladium on activated charcoal 、 18-冠醚-6 、 溶剂黄146 吡啶 、 甲醇 、 氢氧化钾 、 水 、 氢气 、 三乙胺盐酸盐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 6-O-(2,2-dimethylpropanoyl)-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  一些1,2-O-异亚丙基-D-六呋喃糖酯的制备及生物学评价。

  摘要：

  报道了一些带有1,2-O-异亚丙基-d-六呋喃糖功能并且属于3-O-酰基-d-阿糖和6-O-酰基-d-葡萄糖系列的新型糖基酯的合成和生物学评估。 。当比较关于细胞生长抑制的结果时，似乎6-O-酰基-d-葡萄糖衍生物比3-O-酰基-d-阿糖化合物具有更高的活性。在6-O-酰基-d-葡萄糖和3-O-酰基-d-阿洛糖衍生物中，丁酸酯显示出最高的抑制作用。尽管新戊酸酯诱导红细胞分化的程度与先前报道的分子所显示的程度相似，但抑制细胞生长与红细胞分化的高诱导水平无关。中 化学 Lett.1999，9，3153-3158]。

  DOI：

  10.1016/j.carres.2005.12.007

文献信息

• Application of [Mo2(OAc)4] for determination of absolute configuration of pyranoid and furanoid vic-diols by circular dichroism
  作者：Jadwiga Frelek、Zbigniew Pakulski、Aleksander Zamojski

  DOI：10.1016/0957-4166(96)00153-x

  日期：1996.5

  The in situ complexes of [Mo-2(OAc)(4)] with vic-diols obtained from monosaccharides gave CD spectra suitable for determination of absolute configuration in this group. Positive (negative) torsional angle in the O-C-C-O moiety leads to a positive (negative) Cotton effect at around 300 nm. This rule was also extended to vic-diols containing an amino group in the same molecule. Protection of the amino group as a carbamate inhibits the formation of a chiral complex with the NH2 moiety and enables determination of absolute configuration of the diol fragment. Copyright (C) 1996 Elsevier Science Ltd
• Glucose transporter 1-mediated vascular translocation of nanomedicines enhances accumulation and efficacy in solid tumors
  作者：Kazumi Suzuki、Yutaka Miura、Yuki Mochida、Takuya Miyazaki、Kazuko Toh、Yasutaka Anraku、Vinicio Melo、Xueying Liu、Takehiko Ishii、Osamu Nagano、Hideyuki Saya、Horacio Cabral、Kazunori Kataoka

  DOI：10.1016/j.jconrel.2019.02.021

  日期：2019.5

  Nanomedicine modification with ligands directed to receptors on tumor blood vessels has the potential for selectively enhancing nanomedicine accumulation in malignant tissues by overcoming the vascular barrier of tumors. Nevertheless, the development of broadly applicable ligand approaches capable of promoting the transvascular transport of nanomedicines in a wide spectrum of tumors has been elusive so far. By considering the indispensable and persistent glycolytic fueling of tumors, we developed glucose-installed polymeric micelles loading cisplatin (Gluc-CDDP/m) targeting the glucose transporter 1 (GLUT1), which is overexpressed in most tumors and present on vascular endothelial cells, toward improving the delivery efficiency and therapeutic efficacy. The design of the glucose ligands on Gluc-CDDP/m was engineered to control the conjugation via the carbon 6 of the glucose moieties, as well as the ligand density on the poly (ethylene glycol) (PEG) shell of the micelles. The series of micelles was then studied in vitro and in vivo against GLUT1-high human squamous cell carcinoma of the head and neck OSC-19 cells and GLUT1-low human glioblastoma-astrocytoma U87MG cells. Our results showed that precisely tuning the micelles to have glucose ligands on 25% of their PEG chains increased the efficacy against the tumors by significantly enhancing the tumor accumulation, even in GLUT1-low U87MG tumors. The enhancement of the intratumoral levels of these micelles was hindered by concomitant administration of glucose, or the GLUT1 inhibitor STF-31, confirming a GLUT1/glucose-mediated increment of the accumulation. Intravital confocal laser scanning microscopy imaging of tumor tissues further demonstrated the rapid extravasation and penetration of Gluc-CDDP/m in OSC-19 tumors compared to non-targeted CDDP/m. These findings indicate GLUT1-targeting as a promising approach for overcoming the vascular barrier and boosting the delivery of nanomedicine in tumors.
• Preparation and biological evaluation of some 1,2-O-isopropylidene-d-hexofuranose esters
  作者：Giorgio Catelani、Felicia D’Andrea、Martina Landi、Cristina Zuccato、Nicoletta Bianchi、Roberto Gambari

  DOI：10.1016/j.carres.2005.12.007

  日期：2006.3

  The synthesis and biological evaluation of some new glycose esters bearing the 1,2-O-isopropylidene-d-hexofuranose functionality and belonging to the 3-O-acyl-d-allose and 6-O-acyl-d-glucose series are reported. When the results concerning cell growth inhibition are compared, it appears that the 6-O-acyl-d-glucose derivatives are more active than the 3-O-acyl-d-allose compounds. Within both 6-O-acyl-d-glucose

  报道了一些带有1,2-O-异亚丙基-d-六呋喃糖功能并且属于3-O-酰基-d-阿糖和6-O-酰基-d-葡萄糖系列的新型糖基酯的合成和生物学评估。 。当比较关于细胞生长抑制的结果时，似乎6-O-酰基-d-葡萄糖衍生物比3-O-酰基-d-阿糖化合物具有更高的活性。在6-O-酰基-d-葡萄糖和3-O-酰基-d-阿洛糖衍生物中，丁酸酯显示出最高的抑制作用。尽管新戊酸酯诱导红细胞分化的程度与先前报道的分子所显示的程度相似，但抑制细胞生长与红细胞分化的高诱导水平无关。中 化学 Lett.1999，9，3153-3158]。