O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl) trichloroacetimidate | 94715-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl) trichloroacetimidate
• 英文别名: O-(3,4,6-Tri-O-acetyl-2-azido-2-desoxy-α-D-mannopyranosyl)trichloracetimidat；3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl trichloroacetimidate；(2R,3S,4R,5S,6R)-2-(acetoxymethyl)-5-azido-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate；2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-mannose trichloroacetimidate
• CAS: 94715-58-9
• 化学式: C₁₄H₁₇Cl₃N₄O₈
• 分子量: 475.67
• InChiKey: NXSDPOSAOAWHFZ-IYKVGLELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  169.97
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl) trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 octyl 2-azido-2-deoxy-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Modified mannose disaccharides as substrates and inhibitors of a polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase involved in mycobacterial lipoarabinomannan biosynthesis

  摘要：

  A panel of alpha-(1 6)-linked mannose disaccharides (5-8) in which the 2'-OH group has been replaced, independently, by deoxy, fluoro, amino, and methoxy functionalities has been synthesized. Evaluation of these compounds as potential substrates or inhibitors of a polyprenol monophosphomannose-dependent alpha-(1-6)-mannosyltransferase involved in mycobacterial LAM biosynthesis demonstrated that the enzyme is somewhat tolerant substitution at this site. The enzyme recognizes the disaccharides with groups similar or smaller in size than the native hydroxyl (6-8), but not the disaccharide with the more sterically demanding methoxy group (5). The 2'-OH appears not form a critical hydrogen bonding interaction with the protein as the 2'-deoxy analog is a substrate for the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.027
• 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 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl) trichloroacetimidate
  参考文献：
  名称：

  Grundler, Gerhard; Schmidt, Richard R., Liebigs Annalen der Chemie, 1984, # 11, p. 1826 - 1847

  摘要：

  DOI：

文献信息

• Enhancing Potency and Selectivity of a DC‐SIGN Glycomimetic Ligand by Fragment‐Based Design: Structural Basis
  作者：Laura Medve、Silvia Achilli、Joan Guzman‐Caldentey、Michel Thépaut、Luca Senaldi、Aline Le Roy、Sara Sattin、Christine Ebel、Corinne Vivès、Sonsoles Martin‐Santamaria、Anna Bernardi、Franck Fieschi

  DOI：10.1002/chem.201903391

  日期：2019.11.18

  pseudo-dimannoside ligands guided by fragment-based design allowed for the exploitation of an ammonium-binding region in the vicinity of the mannose-binding site of DC-SIGN, leading to the synthesis of a glycomimetic antagonist (compound 16) of unprecedented affinity and selectivity against the related lectin langerin. Here, the computational design of pseudo-dimannoside derivatives as DC-SIGN ligands, their synthesis

  通过基于片段的设计指导对假二金刚烷糖苷配体进行化学修饰，可以利用DC-SIGN甘露糖结合位点附近的铵结合区，从而合成了D-SIGN的拟糖拮抗剂（化合物16）。对相关凝集素langerin具有前所未有的亲和力和选择性。在这里，提出了拟双金刚烷衍生物作为DC-SIGN配体的计算设计，其合成，作为DC-SIGN选择性拮抗剂的评估，DC-SIGN / 16配合物的生物物理表征以及配体活性的结构基础。 。在表征该配体的过程中，晶体内异常的桥连相互作用揭示了DC-SIGN碳水化合物识别域内的可塑性和潜在的二级结合位点。
• Glycosylphosphonates of 2-Amino-2-deoxy-aldoses. Synthesis of a Phosphonate Analogue of Lipid X
  作者：Karin Briner、Andrea Vasella

  DOI：10.1002/hlca.19870700516

  日期：1987.8.12

  A preparation of glycosylphosphonates (27, 28, 36, 38, and 39) from 2-azido-2-deoxy-glycoses (26,35, and 37) and the synthesis of the non-isosteric phosphonate analogue 3a of lipid X(2) are described. The 2-azido group was introduced by azidonitration. Treatment of the 1-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose 22 with 1.5-3 equiv. of P(OMe)3 and 1.2-2.5 equiv. of TfOSiMe3 gave mainly recovered

  的制剂glycOSylphOSphonates的（27，28，36，38，和39，从2-叠氮基-2-脱氧葡糖（）26，35，和37）和非电子等排膦酸酯类似物的合成3A脂质X的（2）进行了说明。通过叠氮化引入2-叠氮基团。用1.5-3当量处理1 - O-乙酰基-2-叠氮基-2-脱氧-β-D-吡喃半乳糖22。P（OMe）3和1.2-2.5当量 TfOSiMe 3的分离得到主要回收的起始原料。在P（OMe）3中作为溶剂，即使在TfOSiMe 3存在下，也可以通过施陶丁格反应获得氨基磷酸二甲酯24。然而，用P（OMe）3和TfOSiMe 3处理苄基化的α-D-半乳糖基-三氯乙酰胺酸酯26，可得到α-和β-D-半乳糖基膦酸酯27和28的1：1混合物，而乙酰化的α -D-葡萄糖-亚氨酸酯35生成α-D-葡萄糖-配置的膦酸酯36。膦酸酯形成的立体选择性与相对容易形成的26和35的氧离子中间体有关。从膦酸
• Direct, microwave-assisted substitution of anomeric nitrate-esters
  作者：D. Jamin Keith、Steven D. Townsend

  DOI：10.1016/j.carres.2017.02.005

  日期：2017.4

  1-nitrate-ester modality for alcohol, alkoxy, and azide coupling partners with minimal purification. While direct glycosylation of nitrate esters ultimately proved unsuccessful, we have demonstrated that an anomeric nitrate-ester can be converted directly to a trichloroacetimidate in a short and simple one-pot procedure, bypassing lower yielding two-step sequences.

  在无试剂的条件下，将一系列在C-3，C-4和C-6位置受保护的碳水化合物2-叠氮基-硝酸盐酯进行热水解。该初步结果已扩展为以最少的纯化将1-硝酸酯-酯形式直接交换为醇，烷氧基和叠氮化物偶联伙伴。虽然最终证明硝酸酯的直接糖基化是不成功的，但我们已经证明，可以在短而简单的一锅法中将异头的硝酸酯直接转化为三氯乙酰亚胺酸酯，而绕过了较低的收率两步法。
• Glycomimetic ligands block the interaction of SARS-CoV-2 spike protein with C-type lectin co-receptors
  作者：Sara Pollastri、Clara Delaunay、Michel Thépaut、Franck Fieschi、Anna Bernardi

  DOI：10.1039/d2cc00121g

  日期：——

  DC-SIGN and its analogue L-SIGN work as co-receptors in many viral infections, including by SARS-CoV-2. Here we describe the first group of small-molecule glycomimetics that bind to L-SIGN, as well as to DC-SIGN, with micromolar affinity.

  DC-SIGN和其类似物L-SIGN在许多病毒感染中作为共受体，包括SARS-CoV-2。在这里，我们描述了第一组与L-SIGN以及DC-SIGN具有微摩尔亲和力的小分子糖类似物的群体。
• The Mild Cleavage of 2-Amino-2-deoxy-<scp>d</scp>-glucoside Methoxycarbonyl Derivatives
  作者：Bryan K. S. Yeung、Sara L. Adamski-Werner、Jennifer B. Bernard、Gaëlle Poulenat、Peter A. Petillo

  DOI：10.1021/ol0063353

  日期：2000.10.1

  [GRAPHICS]The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.