Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-mannopyranoside | 161822-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-mannopyranoside
• 英文别名: [(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-phenylselanyloxan-2-yl]methyl acetate
• CAS: 161822-71-5
• 化学式: C₂₀H₂₅NO₈Se
• 分子量: 486.38
• InChiKey: KAZZJORZKKNMEY-USYVTKNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  丙烯酸叔丁酯 、 Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-mannopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.5h， 以64%的产率得到3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester
  参考文献：
  名称：

  2-氨基-2-脱氧糖的半乳糖，葡萄糖，甘露糖和二糖基C-糖苷。

  摘要：

  [反应：见正文]从易得的前体开始，通过一或两个步骤的方法制备衍生自GalNAc，GlcNAc和ManNAc的硒代糖苷。对异头硒化物进行轻松的C-Se均质分解，以提供相应的异头自由基，这些自由基被烯烃捕获，得到C-糖苷。这提供了基于2-氨基-2-脱氧糖的α-C-糖苷的一般入口，其也适用于二糖变体。

  DOI：

  10.1021/ol0269695
• 作为产物：
  描述：

  2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannopyranose 、 三甲基苯基硒硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以72%的产率得到Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-mannopyranoside
  参考文献：
  名称：

  2-氨基-2-脱氧糖的半乳糖，葡萄糖，甘露糖和二糖基C-糖苷。

  摘要：

  [反应：见正文]从易得的前体开始，通过一或两个步骤的方法制备衍生自GalNAc，GlcNAc和ManNAc的硒代糖苷。对异头硒化物进行轻松的C-Se均质分解，以提供相应的异头自由基，这些自由基被烯烃捕获，得到C-糖苷。这提供了基于2-氨基-2-脱氧糖的α-C-糖苷的一般入口，其也适用于二糖变体。

  DOI：

  10.1021/ol0269695

文献信息

• Seleno glycosides. 2. Synthesis of Phenyl 2-(N-Acetylamino)- and 2-Azido-2-deoxy-1-seleno-.alpha.-D-glycopyranosides via Azido-phenylselenylation of Diversely Protected Glycals
  作者：S. Czernecki、E. Ayadi、D. Randriamandimby

  DOI：10.1021/jo00105a051

  日期：1994.12

  Two methods are described for the preparation of diversely protected phenyl 2-azido-2-deoxy-alpha-D-selenoglycopyranosides from protected glycals. In the first one (method A), a peracetylated glycal is treated with sodium azide and diphenyl diselenide in the presence of (diacetoxyiodo)benzene in dichloromethane at rt. With 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal) an inseparable mixture of phenyl 2-azido-2-deoxy-alpha-gluco- and -alpha-manno-selenoglycosides is obtained (91% yield). With 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (tri-O-acetyl-D-galactal) only the alpha-galacto isomer is obtained (92%). Method A is not compatible with benzyl groups. In method B, a perbenzylated glycal is reacted with trimethylsilyl azide and tetra-n-butylammonium fluoride in the presence of N-phenylselenophthalimide. From protected D-glucal a gluco/manno mixture is obtained, whereas only the galacto isomer is formed from protected D-galactal (75% yield). The compatibility of method B with a variety of protecting groups is exemplified with 6-O-acetyl, 6-O-benzyl, and 6-O-(tert-butyldimethylsilyl)-3,4-O-isopropylidene-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol. The same diastereocontrol is observed, and the alpha-D-galacto isomer is obtained (60-70% yield). Reduction of the azido group of these selenoglycosides with 1,3-propanedithiol in the presence of triethylamine and acetylation affords the corresponding phenyl 2-(N-acetylamino)-2-deoxy-alpha-D-selenoglycopyranosides in goed yield.