2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranose | 18404-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranose
• 英文别名: 2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside；<2-Hydroxy-ethyl>-；[(3R,4S,5R,6R)-4,5-diacetyloxy-6-(2-hydroxyethoxy)oxan-3-yl] acetate
• CAS: 18404-87-0
• 化学式: C₁₃H₂₀O₉
• 分子量: 320.296
• InChiKey: UTZKRSNVJDSZLF-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranose 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到2-(2,3,4-tri-O-acetyl-β-D-xylopyranosyloxy)ethyl(2-cyanoethyl)-(N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y
• 作为产物：
  描述：

  乙二醇 、 2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以66%的产率得到2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranose
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y

文献信息

• [EN] FLUORINATED N-ACETYL GLUCOSAMINE ANALOGS AND XYLOSE DERIVATIVES<br/>[FR] ANALOGUES DE N-ACÉTYL GLUCOSAMINE FLUORÉS ET DÉRIVÉS DE XYLOSE
  申请人：UTI LP

  公开号：WO2019227228A1

  公开（公告）日：2019-12-05

  The present disclosure relates to analogs of N-acetyl glucosamine fluorinated at 4- and/or 6-position(s) and derivatives of xylose at anomeric position for the treatment of a neurological disease, inflammation, cancer and a central nervous system injury.

  本公开涉及N-乙酰葡萄糖胺在4-和/或6-位被氟化的类似物，以及木糖衍生物在缩醛位置用于治疗神经系统疾病、炎症、癌症和中枢神经系统损伤。
• Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides
  作者：Hong-Wen Tao、Xia Wang、Ping-Gui Yi、Zhi-Hong Deng、Xian-Yong Yu、Xiao-Fang Li

  DOI：10.2478/s11696-014-0552-8

  日期：2014.1.1

  was conveniently prepared by a one-pot reaction of per-O-acetylated pyranoses (Ia-If) and 2-(tert-butyldimethylsilyloxy)ethanol (II) with catalysis by BF3·OEt2. The α-(IIIa) or β-linked glycosides (IIIb-IIIf) with 1,2-trans-configuration were obtained from glycosyl donors with participation of the neighbouring 2-O-acetyl group. BF3·OEt2, along with hydrogen fluoride released from BF3·OEt2 under the

  一类立体异构体纯的链烷二醇单糖苷，2-羟乙基per- ø -乙酰基吡喃糖苷（IIIA-IIIF）中，方便地通过的per-一锅反应制备ø -acetylated吡喃糖（图1a-1f）和2- BF 3 ·OEt 2催化的（叔丁基二甲基甲硅烷氧基）乙醇（Ⅱ）。从具有相邻的2- O-乙酰基的糖基供体获得具有1，2-反式构型的α-（IIIa）或β-连接的糖苷（IIIb-IIIf）。BF 3 ·OEt如图2所示，在所使用的实验条件下，氟化硼与从BF 3 ·OEt 2释放的氟化氢一起促进了硅氧烷的后续脱保护，从而成功地提供了2-羟乙基过-O-乙酰基吡喃糖苷。
• Fluorinated N-acetyl glucosamine analogs and xylose derivatives
  申请人：UTI Limited Partnership

  公开号：US11365212B2

  公开（公告）日：2022-06-21

  The present disclosure relates to analogs of N-acetyl glucosamine fluorinated at 4- and/or 6-position(s) and derivatives of xylose at anomeric position for the treatment of a neurological disease, inflammation, cancer and a central nervous system injury.

  本公开涉及在 4-位和/或 6-位上氟化的 N-乙酰葡糖胺类似物和在同分异构位上的木糖衍生物，用于治疗神经系统疾病、炎症、癌症和中枢神经系统损伤。
• “Click” Glycodendrimers Containing 27, 81, and 243 Modified Xylopyranoside Termini
  作者：Jérémy Camponovo、Caroline Hadad、Jaime Ruiz、Eric Cloutet、Sylvain Gatard、Jacques Muzart、Sandrine Bouquillon、Didier Astruc

  DOI：10.1021/jo900554b

  日期：2009.7.17

  A series of large glycodendrimers containing 27, 81, and 243 terminal modified xylose branches from the first (G(1)-27) to the third generation (G(3)-243) were synthesized from 2'-azidoethyl 2,3,4-tri-O-acetyl-beta-D-xylopyranoside and alkynyl-terminated dendrimers by "click" chemistry that is confirmed to be an excellent method to obtain large glyco-dendtimers exemplified by the use of modified xylose. The dendrimers were first characterized by H-1 NMR, C-13H-1} NMR, elemental analysis, and IR spectroscopy. The size progression in the series was also demonstrated using both DOSY NMR and size exclusion chromatography (SEC), the latter technique showing the good polydispersity of all the dendrimers. The size measured by dynamic light scattering (DLS) for the dendrimer G(3)-243 is close to that obtained by the DOSY NMR method.
• FLUORINATED N-ACETYL GLUCOSAMINE ANALOGS AND XYLOSE DERIVATIVES
  申请人：UTI Limited Partnership

  公开号：US20210214384A1

  公开（公告）日：2021-07-15

  The present disclosure relates to analogs of N-acetyl glucosamine fluorinated at 4- and/or 6-position(s) and derivatives of xylose at anomeric position for the treatment of a neurological disease, inflammation, cancer and a central nervous system injury.