(2-hydroxyethyl)-3,4,6-tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranoside | 91611-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-hydroxyethyl)-3,4,6-tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranoside
• 英文别名: (2-Hydroxyethyl)-3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside；2-hydroxyethyl-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
• CAS: 91611-81-3
• 化学式: C₁₄H₂₂O₉
• 分子量: 334.323
• InChiKey: IFBLUFSDHDPYSS-MQYQWHSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2-hydroxyethyl)-3,4,6-tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranoside 在 吡啶 、 甲醇 、 sodium azide 、 水 、 sodium methylate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 2-(iminodiacetato)ethyl-2-deoxy-α-D-arabino-hexopyranoside disodium salt
  参考文献：
  名称：

  Biological evaluation of glucose and deoxyglucose derivatives radiolabeled with [99mTc(CO)3(H2O)3]+ core as potential melanoma imaging agents

  摘要：

  Glucose 9 and 2-deoxyglucose 10 were successfully synthesized and radiolabeled with [(99)mTc(CO)(3)(H2O)(3)](+) intermediate in high yield. The complexes were characterized by HPLC and its stability with histidine over time was challenged. Cell uptake and biodistribution studies in melanoma-bearing C57BL/6 mice were performed. Both compounds showed accumulation in tumor tissue with high tumor-to-muscle ratios. Thus, D-glucose- and D-2-deoxyglucose-Tc-99m complex could be considered as agents for melanoma diagnosis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.106
• 作为产物：
  描述：

  Tri-O-acetyl-D-gulal 、 二乙二醇 在 WPX 800 acid resin 作用下， 以 乙腈 为溶剂， 以40%的产率得到(2-hydroxyethyl)-3,4,6-tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Biological evaluation of glucose and deoxyglucose derivatives radiolabeled with [99mTc(CO)3(H2O)3]+ core as potential melanoma imaging agents

  摘要：

  Glucose 9 and 2-deoxyglucose 10 were successfully synthesized and radiolabeled with [(99)mTc(CO)(3)(H2O)(3)](+) intermediate in high yield. The complexes were characterized by HPLC and its stability with histidine over time was challenged. Cell uptake and biodistribution studies in melanoma-bearing C57BL/6 mice were performed. Both compounds showed accumulation in tumor tissue with high tumor-to-muscle ratios. Thus, D-glucose- and D-2-deoxyglucose-Tc-99m complex could be considered as agents for melanoma diagnosis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.106

文献信息

• Experimental Measurement of Carbohydrate-Aromatic Stacking in Water by Using a Dangling-Ended DNA Model System
  作者：Juan C. Morales、José J. Reina、Irene Díaz、Anna Aviñó、Pedro M. Nieto、Ramón Eritja

  DOI：10.1002/chem.200800335

  日期：2008.9.8

  fundamental importance for a large number of biological processes; carbohydrate-aromatic stacking is a widespread, but poorly understood, structural motif in this recognition. We describe, for the first time, the measurement of carbohydrate-aromatic interactions from their contribution to the stability of a dangling-ended DNA model system. We observe clear differences in the energetics of the interactions

  蛋白质碳水化合物的识别对于许多生物学过程至关重要。在这种认识中，碳水化合物-芳香族堆积是一种广泛的但了解很少的结构基序。我们第一次描述了碳水化合物-芳香族相互作用对悬挂端DNA模型系统稳定性的贡献的测量。我们观察到几种单糖与苯部分相互作用的能量学上存在明显差异，具体取决于羟基数，立体化学和吡喃糖环中甲基的存在。岩藻糖-苯对是所研究系列中最稳定的（-0.4 Kcal mol（-1）），并且该相互作用与其他与蛋白质芳香族残基（例如Phe-Phe， Phe-Met，或Phe-His。涉及的非共价力似乎是分散力和非常规的氢键，而疏水作用似乎并不驱动相互作用。
• Derivatization of Glucose and 2-Deoxyglucose for Transition Metal Complexation: Substitution Reactions with Organometallic99mTc and Re Precursors and Fundamental NMR Investigations
  作者：Jeannine Petrig、Roger Schibli、Cécile Dumas、Roger Alberto、P. A. Schubiger

  DOI：10.1002/1521-3765(20010504)7:9<1868::aid-chem1868>3.0.co;2-h

  日期：2001.5.4

  2-deoxyglucose) and beta-anomer (in case of glucose). Reaction of the sugar derivatives with the organometallic precursor [M(H2O)3(CO)3]+ (M = 99mTc, Re) produced single products in high yield, which are water-soluble and water-stable. The displacement of the three water molecules of the metal precursor and thus the tridentate coordination of the metal-tricarbonyl core exclusively via the amine and the two

  报道了葡萄糖和 2-脱氧葡萄糖在 C-1 位进行双功能化以实现过渡金属配位的合成策略。特别是合成和研究了可能用于诊断核医学的有机金属锝和铼配合物。具体而言，常见的亚氨基二乙酸 (IDA) 部分通过乙烯间隔基团 O-糖苷连接，以产生纯的 α-（在 2-脱氧葡萄糖的情况下）和 β-端基异构体（在葡萄糖的情况下）。糖衍生物与有机金属前体 [M(H2O)3(CO)3]+ (M = 99mTc, Re) 的反应以高产率产生了水溶性和水稳定性的单一产品。金属前体的三个水分子的置换以及金属-三羰基核的三齿配位仅通过胺和 IDA 螯合物的两个羧酸官能团通过 1D 和 2D 1H NMR 光谱、质谱法验证, 和红外光谱。放射性标记的产品 (99mTc) 在生理磷酸盐缓冲液 (pH = 7.4) 和人血浆中在 37 摄氏度的 24 小时内证明了它们在体外具有出色的稳定性。
• Synthèse d'un 2-désoxy-spiro-orthoester anomérique
  作者：Gérard Descotes、Hamid Idmoumazet Jean-Pierre Praly

  DOI：10.1016/0008-6215(84)85341-0

  日期：1984.6

  Synthese du O-[desoxy-2 tri-«O»-acetyl D-arabino-hexopyranosylidene]-1,2 ethanediol-1,2 a partir de tri-O-acetyl D-glucal

  O- [脱氧-2三-O-乙酰基D-阿拉伯糖基-己吡喃次亚烷基] -1，2-乙二醇-1，2-三-O-乙酰基D-葡糖基的合成