methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside | 160636-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• 英文别名: methyl 2-azido-2-deoxy-4,6-benzylidene-α-D-glucopyranoside；(2R,4aR,6S,7R,8R,8aS)-7-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 160636-37-3
• 化学式: C₁₄H₁₇N₃O₅
• 分子量: 307.306
• InChiKey: WCSBCLMCXJSBOJ-UQPQVDFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 sodium hydride 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  [EN] AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
  [FR] PROCÉDÉ EFFICACE ET EXTENSIBLE DE FABRICATION DE FONDAPARINUX SODIQUE

  摘要：

  本发明涉及一种用于合成因子Xa抗凝剂Fondaparinux及相关化合物的过程。此外，该发明还涉及用于合成Fondaparinux及相关化合物的各种中间体的高效可扩展过程。

  公开号：

  WO2013115817A1
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 盐酸 、 4-二甲氨基吡啶 、 triflic azide 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors

  摘要：

  Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.020

文献信息

• Synthetic heparin pentasaccharides
  申请人：ALCHEMIA LIMITED

  公开号：US09243018B2

  公开（公告）日：2016-01-26

  Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.

  合成单糖，双糖，三糖，四糖和五糖的制备和使用，用于合成肝素类化合物的制备。
• Oligo-Aminosaccharide compound
  申请人：Wada Takeshi

  公开号：US20110003980A1

  公开（公告）日：2011-01-06

  An oligo-aminosaccharide compound formed by binding 3 to 6 saccharides, such as 2,6-diamino-2,6-dideoxy-α-(1→4)-D-glucopyranose oligomers, or a salt thereof, which has high affinity to a double-stranded nucleic acid.

  由3到6个糖苷结合形成的寡糖氨基酸化合物，例如2,6-二氨基-2,6-二去氧-α-(1→4)-D-葡萄糖吡喃糖寡聚体，或其盐，具有高亲和力双链核酸。
• Synthesis and two-dimensional nuclear magnetic resonance analysis of a tetra- and a hexa-saccharide fragment of the O-specific polysaccharide of Shigella dysenteriae type 1
  作者：Vince Pozsgay、Bruce Coxon

  DOI：10.1016/0008-6215(94)80035-9

  日期：1994.5

  The synthesis of the tetra- and hexa-saccharide methyl glycosides alpha-D-Galp-(1-->3)-alpha-D-GlcpNAc-(1-->3)-alpha-L-Rhap-(1-->3)- alpha-L-Rhap- OMe (1), and alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->2)-alpha-D-Galp-(1--> 3)-alpha-D-GlcpNAc- (1-->3)-alpha-L-Rhap-(1-->3)-alpha-L-Rhap-OMe (3) is described, which represent various epitopes of the O-specific polysaccharide of Shigella dysenteriae type 1.

  6-四-O-苄基-1-硫代-β-D-吡喃半乳糖苷（16）和2-叠氮基-4,6-O-亚苄基-3-O-溴乙酰基-2-脱氧-β-D-吡喃葡萄糖基氯（19）。对寡糖1和3的1H和13C NMR光谱进行的详细分析证实，六糖3比1或同源五糖41更好地接近天然多糖的构象。
• Synthesis and biological evaluation of analogues of bacterial lipid I
  作者：Domingos J. Silva、Caryn L. Bowe、Arthur A. Branstrom、Eugene R. Baizman、Michael J. Sofia

  DOI：10.1016/s0960-894x(00)00583-7

  日期：2000.12

  Bacterial Lipid I analogues containing different anomeric groups at the muramic acid moiety were synthesized and screened in MurG enzyme assays run in the presence and absence of cell wall membranes. The results obtained in this study help elucidate the role of the lipid diphosphate in the recognition of Lipid I by MurG.
• Synthesis of Oligodiaminosaccharides Having α-Glycoside Bonds and Their Interactions with Oligonucleotide Duplexes
  作者：Rintaro Iwata、Masafumi Sudo、Kenta Nagafuji、Takeshi Wada

  DOI：10.1021/jo200951p

  日期：2011.8.5

  Syntheses of the novel oligodiaminosaccharides, alpha-(1 -> 4)linked-2,6-diamino-2,6-dideoxy-D-glucopyranose oligomers, and their interactions with nucleic acid duplexes DNA-DNA, RNA-RNA, and DNA-RNA are described. Monomers to tetramers of oligodiaminoglucose derivatives having alpha-glycosyl bonds were successfully synthesized using a chain elongation cycle including glycosylation reactions of a 6-phthalimide glycosyl donor. UV melting experiments for a variety of nucleic acid duplexes in the absence and presence of the oligodiaminosaccharides were performed. The synthesized oligodiaminosaccharides exhibited notable thermodynamic stabilization effects on A-type RNA-RNA and DNA-RNA duplexes, whereas B-type DNA-DNA duplexes were not stabilized by the synthesized oligodiaminosaccharides. Among the oligodiaminosaccharides, the tetramer exhibited the highest ability to stabilize A-type duplexes, and the increase in T(m) values induced by the tetramer were higher than those induced by neomycin B and tobramycin, which are known aminoglycosides having ability to bind and stabilize a variety of RNA molecules. CD spectrometry experiments revealed that the oligodiaminosaccharides caused small structural changes in RNA-RNA duplexes, whereas no appreciable changes were observed in the structure of DNA-DNA duplexes. ITC (isothermal titration calorimetry) experiments demonstrated that the amount of heat generated by the interaction between RNA-RNA duplexes and the tetradiaminosaccharides was approximately double that generated by that between DNA-DNA duplexes and the tetradiaminosaccharides. These results strongly suggested the existence of an A-type nucleic acid specific-binding mode of the oligodiaminosaccharides, which bind to these duplexes and cause small structural changes.