3-formylpropyl 2-deoxy 2-N-acetyl 3-O-(β-D-glucopyranosyluronate)-β-D-glucopyranoside | 537006-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-formylpropyl 2-deoxy 2-N-acetyl 3-O-(β-D-glucopyranosyluronate)-β-D-glucopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-(4-oxobutoxy)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 537006-95-4
• 化学式: C₁₈H₂₉NO₁₃
• 分子量: 467.427
• InChiKey: NZRRUUPOEHVYBN-VZEFLDEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  222
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙二胺 、 3-formylpropyl 2-deoxy 2-N-acetyl 3-O-(β-D-glucopyranosyluronate)-β-D-glucopyranoside 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2-[4-[2-[4-[(2R,3R,4R,5S,6R)-3-acetamido-4-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutylamino]ethylamino]butoxy]-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of hyaluronan-mimetic gemini disaccharides

  摘要：

  An efficient strategy has been designed for the preparation of synthetic mimics of hyaluronan (RA, 1) and its dimerized (Gemini) disaccharides (2a,b) via n-pentenyl glycoside formation. Construction of the target molecules was achieved through a combination of protection/deprotection protocols, imidate glycosylation methodology followed by ozonolysis, and reductive amination. These tailored synthetic mimics could act as versatile building blocks with therapeutic applications in tissue engineering, treatment of cancer and as drug delivery agents. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01567-3
• 作为产物：
  描述：

  3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 臭氧 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 54.5h， 生成 3-formylpropyl 2-deoxy 2-N-acetyl 3-O-(β-D-glucopyranosyluronate)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a hyaluronan neoglycopolymer by ring-opening metathesis polymerizationElectronic supplementary information (ESI) available: spectral data for compound 11, glycomonomer 14 and glycopolymer [A]. See http://www.rsc.org/suppdata/cc/b3/b301734f/

  摘要：

  一种源自透明质酸（HA）的二糖被合成，其带有n-戊烯间隔臂，这促进了二糖与降冰片烯模板之间的衍生化。随后，单体的环开异构聚合反应生成了低多分散性的HA类似物新糖聚合物。

  DOI：

  10.1039/b301734f

文献信息

• Hyaluronan-based glycoclusters as probes for chemical glycobiology
  作者：Shyam M. Rele、Suri S. Iyer、Elliot L. Chaikof

  DOI：10.1016/j.tetlet.2007.05.097

  日期：2007.7

  A strategy is described for the synthesis of beta-(l,3)-GlcA-GlcNAc dimeric and tetrameric glycoclusters through the conjugation of disaccharide groups onto. a diaminodiamide aromatic scaffold by reductive amination. (C) 2007 Elsevier Ltd. All rights reserved.
• Design and synthesis of hyaluronan-mimetic gemini disaccharides
  作者：Suri S Iyer、Shyam M Rele、S Baskaran、Elliot L Chaikof

  DOI：10.1016/s0040-4020(02)01567-3

  日期：2003.1

  An efficient strategy has been designed for the preparation of synthetic mimics of hyaluronan (RA, 1) and its dimerized (Gemini) disaccharides (2a,b) via n-pentenyl glycoside formation. Construction of the target molecules was achieved through a combination of protection/deprotection protocols, imidate glycosylation methodology followed by ozonolysis, and reductive amination. These tailored synthetic mimics could act as versatile building blocks with therapeutic applications in tissue engineering, treatment of cancer and as drug delivery agents. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of a hyaluronan neoglycopolymer by ring-opening metathesis polymerizationElectronic supplementary information (ESI) available: spectral data for compound 11, glycomonomer 14 and glycopolymer [A]. See http://www.rsc.org/suppdata/cc/b3/b301734f/
  作者：Suri Iyer、Shyam Rele、Gabriela Grasa、Steven Nolan、Elliot L. Chaikof

  DOI：10.1039/b301734f

  日期：——

  A hyaluronan (HA)-derived disaccharide was synthesized bearing an n-pentenyl spacer arm, which facilitated disaccharide derivatization with a norbornene template. Subsequent ring opening metathesis polymerization of the monomer produced an HA-mimetic neoglycopolymer of low polydispersity.

  一种源自透明质酸（HA）的二糖被合成，其带有n-戊烯间隔臂，这促进了二糖与降冰片烯模板之间的衍生化。随后，单体的环开异构聚合反应生成了低多分散性的HA类似物新糖聚合物。