methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-selenononulopyranosid)onate | 131569-89-6

• 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: methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-selenononulopyranosid)onate
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-phenylselanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 131569-89-6
• 化学式: C₂₆H₃₃NO₁₂Se
• 分子量: 630.508
• InChiKey: JYWQXBNLXKVLPW-UQJVNAJPSA-N

物化性质

• 沸点：
  675.5±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-selenononulopyranosid)onate 生成 (2S,4S,5R,6R)-5-乙酰氨基-4-羟基-2-苯基硒基-6-[(1R,2R)-1,2,3-三羟基丙基]四氢吡喃-2-羧酸
  参考文献：
  名称：

  Phase-transfer-catalyzed synthesis of a phenylseleno α-ketoside of N-acetylneuraminic acid, (phenyl 5-acetamido-3,5-dideoxy-d-glycero-α-d-galacto-2-selenononulopyranosid)-onic acid; a new sialidase inhibitor

  摘要：

  DOI：

  10.1016/0008-6215(90)80105-c
• 作为产物：
  描述：

  (2Z)-2-[[5-(3,4-二甲基-5-硝基苯基)-2-呋喃基]亚甲基]-7-甲基-3-氧代-5-苯基-5H-噻唑并[3,2-a]嘧啶-6-羧酸乙酯 、 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 苄基三乙基氯化铵 作用下， 以 sodium hydroxide 、 氯仿 为溶剂， 反应 0.42h， 以60%的产率得到methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-selenononulopyranosid)onate
  参考文献：
  名称：

  Phase-transfer-catalyzed synthesis of a phenylseleno α-ketoside of N-acetylneuraminic acid, (phenyl 5-acetamido-3,5-dideoxy-d-glycero-α-d-galacto-2-selenononulopyranosid)-onic acid; a new sialidase inhibitor

  摘要：

  DOI：

  10.1016/0008-6215(90)80105-c

文献信息

• Use of Phenyl 2-α-Selenoglycosides of N-Acetylneuraminic Acid as a Glycosyl Donor for the Glycosylation Reactions
  作者：Kiyoshi Ikeda、Yuji Sugiyama、Kiyoshi Tanaka、Masayuki Sato

  DOI：10.1016/s0960-894x(02)00400-6

  日期：2002.9

  Phenyl 2-alpha-selenoglycosides of Neu5Ac were successfully prepared from the corresponding peracetylated chloro derivative of Neu5Ac 1 and phenylselenol in the presence of N,N-di-isopropylethylamine in excellent yields. The reaction of with various alcohols was effectively catalyzed by NIS/TfOH or DMTST to produce a variety of glycosides in moderate yields. Selective activation of over phenyl 2-alpha-thioglycoside

  在N，N-二异丙基乙胺存在下，由Neu5Ac 1和苯硒酚的相应的过乙酰化氯代衍生物成功制备了Neu5Ac的苯基2-α-硒代糖苷。NIS / TfOH或DMTST有效地催化了与各种醇的反应，从而以中等收率产生了多种糖苷。还实现了Neu5Ac的苯基2-α-硫代糖苷与AgOTf / K（2）CO（3）的选择性活化。
• Indium(I) iodide mediated efficient synthesis of selenoglycosides
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2006.02.009

  日期：2006.4

  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.