phenyl 2,3,4-tri-O-acetyl-1-seleno-α-L-rhamnopyranoside | 136809-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-acetyl-1-seleno-α-L-rhamnopyranoside
• 英文别名: phenyl 2,3,4-tri-O-acetyl-1-seleno-β-L-rhamnopyranoside；[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-2-methyl-6-phenylselanyloxan-3-yl] acetate
• CAS: 136809-99-9
• 化学式: C₁₈H₂₂O₇Se
• 分子量: 429.328
• InChiKey: GKSVPKIDNZPSNR-VVRBALCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-1-seleno-α-L-rhamnopyranoside 、 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyI-(1->3)-2-O-benzoyl-4,6-O-benzylidene-O-α-D-gluco-pyranoside
  参考文献：
  名称：

  苯基硒代糖苷是新型的通用糖基供体。硫糖苷的选择性活化

  摘要：

  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。

  DOI：

  10.1016/0040-4039(91)80005-q
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 、 苯硒酚 在 三氟化硼乙醚 作用下， 生成 phenyl 2,3,4-tri-O-acetyl-1-seleno-α-L-rhamnopyranoside
  参考文献：
  名称：

  苯基硒代糖苷是新型的通用糖基供体。硫糖苷的选择性活化

  摘要：

  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。

  DOI：

  10.1016/0040-4039(91)80005-q

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。
• 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。
• 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。
• Novel glycosidation methodology. The use of phenyl selenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis
  作者：Seema Mehta、B. Mario Pinto

  DOI：10.1021/jo00064a012

  日期：1993.6

  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.
• Tris(4-bromophenyl)aminium hexachloroantimonate-mediated glycosylations of selenoglycosides and thioglycosides. Evidence for single electron transfer?11This paper is dedicated, with respect and gratitude, to the memory of Margaret A. Clark.
  作者：Seema Mehta、B.Mario Pinto

  DOI：10.1016/s0008-6215(98)00163-3

  日期：1998.8

  Radical cation-initiated glycosylation reactions of phenyl selenoglycosides are described. Glycosylations of phenyl selenoglycosides effected by the single-electron-transfer (SET) reagent, tris(4-bromophenyl)aminium hexachloroantimonate (BAHA), are examined with primary and secondary hydroxyl accepters. The corresponding reaction of an ethyl thioglycoside with a primary hydroxyl acceptor is also examined. Reactions are performed in the presence of the SET quenching reagent, 1,2,4,5-tetramethoxybenzene, to assess whether BAHA-mediated glycosylation reactions involve SET. These experiments indicate that the reactions are completely quenched in dichloromethane but only partially in acetonitrile. The results provide support for the SET mechanism but an alternative mechanism involving electrophilic activation cannot be discounted. The oxidation potentials of various selenoglycosides are determined by cyclic voltammetry. (C) 1998 Elsevier Science Ltd. All rights reserved.