3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate | 94715-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl) trichloroacetimidate；2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate；2-azido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate；3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-trichloroacetimido-α-D-glucopyranoside；3,4,6-tetra-O-acetyl-2-deoxy-2-azido-α-D-glucopyranosyl trichloroacetimidate；(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-azido-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate；3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranoside trichloroacetimidate；3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichioroacetimidate；trichloroacetimido-3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-glucopyranoside；--Lucopyranose,2-zido-2-eoxy-,3,4,6-riacetate1-(2,2,2-richloroethanimidat)；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-azido-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 94715-56-7
• 化学式: C₁₄H₁₇Cl₃N₄O₈
• 分子量: 475.67
• InChiKey: NXSDPOSAOAWHFZ-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 O-(2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3:4,5-di-O-cyclohexylidene-1-O-(1R)-menthyloxycarbonyl-D-myoinositol
  参考文献：
  名称：

  从克氏锥虫的脂质中含有不饱和脂肪酸的生物活性糖基磷脂酰肌醇的化学合成。

  摘要：

  DOI：

  10.1002/anie.200502779
• 作为产物：
  描述：

  [(2R,3S,4R)-3,4-diacetyloxy-5-azido-6-nitrooxyoxan-2-yl]methyl acetate 在 potassium carbonate 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  First Total Synthesis of Mycothiol and Mycothiol Disulfide

  摘要：

  The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-alpha,beta-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.

  DOI：

  10.1021/ol0362008

文献信息

• [EN] OLIGOSACCHARIDE COMPOUNDS FOR USE IN MOBILISING STEM CELLS<br/>[FR] COMPOSÉS D'OLIGOSACCHARIDE POUR UTILISATION DANS LA MOBILISATION DE CELLULES SOUCHES
  申请人：ENDOTIS PHARMA

  公开号：WO2010029185A1

  公开（公告）日：2010-03-18

  A compound of the following formula or a salt, solvate or formula (I) and a pharmaceutical composition containing said compound. It concerns also its use in the treatment of cancer and/or of pathological angiogenesis and/or in promoting the mobilisation of stem cells, in particular hematopoietic stem cells.

  以下化学式的化合物或盐、溶剂化合物或化学式（I）以及含有该化合物的药物组合物。它还涉及其在治疗癌症和/或病理性血管生成和/或促进干细胞动员，特别是造血干细胞方面的用途。
• [EN] HEPARANASE COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS HÉPARANASE ET MÉTHODES D'UTILISATION
  申请人：UNIV FLORIDA

  公开号：WO2020219753A1

  公开（公告）日：2020-10-29

  The invention relates to compounds that interact with heparanase, uses in heparanase screening, uses in in vitro and in vivo imaging (e.g., positron emission tomography (PET) and magnetic resonance imaging (MRI)), methods of synthesis, methods of modulating heparanase activity, and methods of treating disease and disorders associated with heparanase. The compounds of the invention are also useful in treating one or more diseases or disorders associated with the function of heparanase.

  这项发明涉及与肝素酶相互作用的化合物，用于肝素酶筛选，用于体外和体内成像（例如正电子发射断层扫描（PET）和磁共振成像（MRI）），合成方法，调节肝素酶活性的方法，以及治疗与肝素酶相关的疾病和疾病的方法。该发明的化合物还可用于治疗与肝素酶功能相关的一个或多个疾病或疾病。
• Nickel-Catalyzed Stereoselective Glycosylation with C(2)-<i>N</i>-Substituted Benzylidene <scp>d</scp>-Glucosamine and Galactosamine Trichloroacetimidates for the Formation of 1,2-<i>cis</i>-2-Amino Glycosides. Applications to the Synthesis of Heparin Disaccharides, GPI Anchor Pseudodisaccharides, and α-GalNAc
  作者：Enoch A. Mensah、Fei Yu、Hien M. Nguyen

  DOI：10.1021/ja106682m

  日期：2010.10.13

  α-selectivity. The reactive sites of the nucleophiles or the nature of the protecting groups have little effect on the α-selectivity. This methodology has also been successfully applied to both disaccharide donors and acceptors to provide the corresponding oligosaccharides in high yields and α-selectivity. The efficacy of the nickel procedure has been further applied toward the preparation of heparin disaccharides

  1,2-cis-2-amino glycosides 是在各种生物学上重要的寡糖和糖肽中发现的关键成分。尽管 1,2-cis-2-氨基糖苷的合成取得了显着进展，但目前最先进方法的缺点包括底物范围有限、产率低、反应时间长和异头混合物。我们开发了一种通过镍催化的 α-选择性糖基化与 C(2)-N-取代的亚苄基 D-葡糖胺和半乳糖胺三氯乙酰亚胺合成 1,2-顺-2-氨基糖苷的新方法。这些糖基供体能够与多种醇偶联，以高产率提供具有出色 α 选择性的糖缀合物。此外，仅需要亚化学计量的镍 (5-10 mol%) 才能在 25 °C 下进行反应。目前的镍方法依赖于镍配体配合物的性质来控制 α 选择性。亲核试剂的反应位点或保护基团的性质对α-选择性几乎没有影响。该方法也已成功应用于二糖供体和受体，以高产率和 α 选择性提供相应的寡糖。镍过程的功效已进一步应用于制备肝素二糖、GPI 锚定假二糖和 α-Glu
• Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors
  作者：Mahipal Yadav、Riya Raghupathy、Varma Saikam、Saidulu Dara、Parvinder Pal Singh、Sanghapal D. Sawant、Satyajit Mayor、Ram A. Vishwakarma

  DOI：10.1039/c3ob42116c

  日期：——

  Synthesis of first generation non-hydrolysable C-phosphonate GPI analogs, viz., 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-O-(sn-3,4-bis(palmitoyloxy)butyl-1-phosphonate) 23a and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-O-(sn-2,3-bis(palmitoyloxy)propyl-1-phosphonate) 23b, is reported. The target compounds were synthesized by the coupling of α-pseudodisaccharide 21 with

  第一代不可水解的C-GPI膦酸酯类似物，合成v IZ，6-。ø - （2-氨基-2-脱氧-3-α- d吡喃葡萄糖基） - d -肌醇肌醇-1- Ö - （SN - 3,4-双（棕榈酰氧基）丁基-1-膦酸盐）23A和6- ø - （2-氨基-2-脱氧-3-α- d吡喃葡萄糖基） - d -肌醇肌醇-1- ö - （SN -2据报道，（3-双（棕榈酰氧基）丙基-1-膦酸酯）23b。通过将α-假二糖21与膦酸偶联来合成目标化合物分别以定量收率得到18a和18b，然后脱保护。这些合成的C-膦酸酯GPI探针对磷脂酰肌醇特异性磷脂酶C（PI-PLC）具有抗性，并且还显示出对酶活性的中等抑制作用。
• Synthesis of mono- and disaccharide analogs of moenomycin and lipid II for inhibition of transglycosylase activity of penicillin-binding protein 1b
  作者：Sylvie Garneau、Lei Qiao、Lan Chen、Suzanne Walker、John C. Vederas

  DOI：10.1016/j.bmc.2004.09.019

  日期：2004.12

  Three types of mono- and disaccharides 3a,b, 4a-c, 5, and some chaetomellic acid A analogs 6 and 42-44 were synthesized as potential inhibitors of the transglycosylase activity of penicillin-binding protein 1b (PBP1b), a key bacterial enzyme responsible for the formation of the polysaccharide backbone of peptidoglycan as well as for cross-linking of its peptide portions. The target compounds combine

  合成了三种类型的单糖和二糖3a，b，4a-c，5和一些chaetomellic acid A类似物6和42-44，它们可能是关键细菌青霉素结合蛋白1b（PBP1b）的糖基转移酶活性的抑制剂。负责肽聚糖多糖主链形成及其肽部分交联的酶。目标化合物结合了莫诺霉素活性部分和天然PBP1b底物脂质II的结构特征。以收敛的方式获得所需的骨架，该方式涉及将脂烷基化的甘油酸部分11a，b连接至相应的含碳水化合物的膦酸23、24a和24b。制备化合物3a，b以验证糖与不可裂解的C-膦酸酯部分之间的距离要求。合成了化合物4a-c，以检验moenomycin的第一个糖单元（一种已知的PBP1b转糖基酶催化抑制剂）相对于抗生素活性的重要性。它们是通过以下方法制备的：将11a，b与28a和28c缩合，这些缩合是通过将3-溴丙醇与恶唑啉25a，b糖基化，然后将Arbuzov与亚磷酸三乙酯或亚磷酸三甲酯反应，然后再与溴