phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-gluco-pyranoside | 23661-29-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-gluco-pyranoside
• 英文别名: I+/--D-Glucopyranoside, phenyl 1-seleno-, tetraacetate；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-phenylselanyloxan-2-yl]methyl acetate
• CAS: 23661-29-2
• 化学式: C₂₀H₂₄O₉Se
• 分子量: 487.365
• InChiKey: BZEPSHSXWNWSCD-OUUBHVDSSA-N

物化性质

• 沸点：
  520.2±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 indium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以92%的产率得到phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-gluco-pyranoside
  参考文献：
  名称：

  Indium(I) iodide mediated efficient synthesis of selenoglycosides

  摘要：

  A convenient odorless methodology has been developed for the preparation of selenoglycosides through indium(l) iodide mediated cleavage of diselenides and reaction with glycosyl bromides. The yields were excellent in all cases. Retention of the configuration at the anomeric center was observed in each case. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.009

文献信息

• Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy
  作者：Peng Ji、Yueteng Zhang、Feng Gao、Fangchao Bi、Wei Wang

  DOI：10.1039/d0sc04136j

  日期：——

  transfer pathway have dictated glycosylation development, the direct glycosylation of readily accessible glycosyl donors as radical precursors is particularly appealing because of high radical anomeric selectivity and atom- and step-economy. However, the development of the radical process has been challenging owing to notorious competing reduction, elimination and/or SN side reactions of commonly used

  虽然涉及 2e -转移途径的策略决定了糖基化的发展，但由于自由基异头选择性高以及原子和步骤经济性，易于获得的糖基供体作为自由基前体的直接糖基化特别有吸引力。然而，由于常用的不稳定糖基供体的竞争性还原、消除和/或 S N副反应，自由基过程的发展一直充满挑战。在这里，我们介绍了一种有机光催化策略，通过光氧化还原介导的 HAT 催化，糖基溴可以有效地转化为相应的异头自由基，无需过渡金属或导向基团，并实现高度异头选择性。温和的反应条件能够合成具有挑战性的α-1,2-顺式硫代糖苷、各种官能团的耐受性以及常见戊糖和己糖的广泛底物范围，证明了该平台的强大功能。此外，这种通用方法与 sp 2和 sp 3硫亲电子试剂以及总共探测的 50 种底物的后期糖基多样化兼容。
• 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.