phenyl 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-l-seleno-β-D-glucopyranoside | 136810-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: phenyl 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-l-seleno-β-D-glucopyranoside
• 英文别名: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-seleno-β-D-glucopyranoside；Phenyl 3,4,6-tri-o-acetyl-2-deoxy-2-phthalimido-beta-d-selenoglucopyranoside；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-phenylselanyloxan-2-yl]methyl acetate
• CAS: 136810-00-9
• 化学式: C₂₆H₂₅NO₉Se
• 分子量: 574.446
• InChiKey: MXNZDMFUTBLYFF-HDXRJONQSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  652.6±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-l-seleno-β-D-glucopyranoside 在 水 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以87%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose
  参考文献：
  名称：

  Novel glycosidation methodology. The use of phenyl selenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis

  摘要：

  The use of phenyl selenoglycosides as glycosyl donors and acceptors in glycosidation reactions is described. The versatility of these novel compounds is illustrated by the selective activation of both ''disarmed'' and ''armed'' phenyl selenoglycoside donors over ''armed'' ethyl thioglycoside acceptors with silver trifluoromethanesulfonate in the presence of potassium or silver carbonate to give disaccharides in excellent yield. Selective activation of glycosyl bromide donors over phenyl selenoglycoside acceptors is realized by silver trifluoromethanesulfonate promotion in the presence of collidine. Such selectivity is also demonstrated by the activation of a glycosyl trichloroacetimidate donor in the presence of selenoglycoside acceptors with triethylsilyl trifluoromethanesulfonate. The central role of selenoglycosides is illustrated by the synthesis of a trisaccharide that profits from the sequential, selective activation of a glycosyl bromide donor over a selenoglycoside acceptor and the resulting disaccharide selenoglycoside over a thioglycoside acceptor. The liberation of the anomeric hydroxyl group from a phenyl selenoglycoside is also described.

  DOI：

  10.1021/jo00064a012
• 作为产物：
  描述：

  苯酐 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 phenyl 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-l-seleno-β-D-glucopyranoside
  参考文献：
  名称：

  碘基苯促进的硒糖苷糖基化：在一锅糖基化中的应用

  摘要：

  开发了一种由碘酰苯激活的硒代糖苷糖基化的新方法。该糖基化反应条件温和、快速、高效，对多种保护基具有较高的耐受性，底物范围广，有利于合成复杂糖苷。此外，在碘酰苯的促进下，硒代糖苷与硫代糖苷具有正交性。值得注意的是，通过乙酰基保护的硒代糖苷获得了高产率的低反应性葡萄糖醛酸化反应产物。最后，β-(1→6)低聚糖的正交一锅合成证明了该方法在低聚糖合成中的有用性。

  DOI：

  10.1021/acs.orglett.4c00653

文献信息

• InBr3-Catalyzed Synthesis of Aryl 1,2-trans-Thio(seleno)glycosides
  作者：Lan Yu、Weihua Xue、Teng Ma、Changwei Li、Haijing Liang、Zhaoyan Wang

  DOI：10.1055/s-0036-1588507

  日期：2017.10

  InBr3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2-trans-stereoselectivity. This bromide is an air- and moisture-stable Lewis acid and therefore the reactions can be performed in air atmosphere making the procedure simple to perform.

  InBr3被证明是一种高效的催化剂，可在室温下与芳基巯基或硒酚完全乙酰化的醛糖反应中迅速生成相应的巯基糖或硒基糖，且具有纯粹的1,2-反式选择性。这种溴化物是一种空气和湿气稳定的路易斯酸，因此反应可以在空气氛围中进行，使得操作程序简单。
• Phenylselenoglycosides as novel, versatile glycosyl donors. Selective activation over thioglycosides
  作者：Seema Mehta、B. Mario Pinto

  DOI：10.1016/0040-4039(91)80005-q

  日期：1991.1

  of phenylselonoglycosides over ethylthioglycosides with silver trifluoromethanesulfonate and anhydrous potassium carbonate gives an efficient synthesis of disaccharides from selenoglycoside donors and thioglycoside acceptors. Activation is quenched by addition of 1,1,3,3,-tetramethylurea or collidine.

  用三氟甲磺酸银和无水碳酸钾对乙基巯基糖苷在乙基硫代糖苷上的选择性活化，可以从硒代糖苷供体和硫代糖苷受体高效合成二糖。通过添加1,1,3,3，-四甲基脲或可力丁淬灭活化。
• Odorless Eco-Friendly Synthesis of Thio- and Selenoglycosides in Ionic Liquid
  作者：Anup Misra、Abhijit Sau

  DOI：10.1055/s-0030-1260966

  日期：2011.8

  condition, the reductive cleavage of disulfidesand di-selenides using triethylsilane and borontrifluoridediethyletherate combination followed by the reaction of the in situgenerated -thiolate and selenoetes with glycosyl acetatederivatives in recyclable room-temperature ionic liquid, [BMIM]˙BF 4 resultedin excellent yields of thio- and selenoglycosides avoiding the useof obnoxious thiols/selenols and metallic

  报告了一种用于制备 1,2-反式硫代糖苷和硒糖苷的环保无味方法。在一锅条件下，使用三乙基硅烷和三氟化硼二乙基醚合物的组合还原裂解二硫化物和二硒化物，然后原位生成的硫醇盐和硒化物与醋酸糖基衍生物在可回收的室温离子液体中反应，得到 [BMIM]˙BF 4硫醇和硒糖苷的优异收率，避免使用有害的硫醇/硒醇和金属催化剂。
• Elimination reactions of glycosyl selenoxides
  作者：David J. Chambers、Graham R. Evans、Antony J. Fairbanks

  DOI：10.1016/j.tet.2004.07.005

  日期：2004.9

  Glycosyl selenoxides, generated in situ from selenoglycosides by a Sharpless-type oxidation, undergo facile syn elimination leading to 2-hydroxy and 2-amino glycals in high yield.

  糖苷亚硒酸酯是通过Sharpless型氧化从硒代糖苷原位生成的，可以轻松地进行syn消除，从而以高收率得到2-羟基和2-氨基糖基。
• Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides
  作者：Chinmoy Mukherjee、Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2005.11.074

  日期：2006.1

  A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. The yields were excellent in all cases.

  已经设计了一种方便的无味方法，用于通过锌介导的二硫化物和二硒化物的裂解以及原位形成的硫醇盐和硒化物与糖基溴化物的反应来制备1,2-反式-硫代和硒代糖苷。在所有情况下，收率都非常好。