Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-galactopyranoside | 161822-74-8

• 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-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-phenylselanyloxan-2-yl]methyl acetate
• CAS: 161822-74-8
• 化学式: C₂₀H₂₅NO₈Se
• 分子量: 486.38
• InChiKey: KAZZJORZKKNMEY-OUUBHVDSSA-N

物化性质

• 沸点：
  610.9±55.0 °C(predicted)

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：

  Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-galactopyranoside 在 三乙基硼 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 2-acetamido-3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-galactopyranose
  参考文献：
  名称：

  基于N-酰基半乳糖胺的自由基介导的α-C-糖苷合成。

  摘要：

  [结构] N-酰基2-氨基-2-脱氧半乳糖（酰基= MeCO，CF（3）CO，t-BuOCO）的C-糖苷可通过用活化的烯烃捕获异头基团以立体选择性方式获得。使用异头硒化物，在避免竞争性还原的条件下进行自由基的产生和捕获，并且该化学方法已用于合成O-苄基α-D-GalNAc的新型C-糖苷类似物。

  DOI：

  10.1021/ol006682c
• 作为产物：
  描述：

  二苯基二硒醚 在 sodium azide 、 碘苯二乙酸 作用下， 生成 Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  基于N-酰基半乳糖胺的自由基介导的α-C-糖苷合成。

  摘要：

  [结构] N-酰基2-氨基-2-脱氧半乳糖（酰基= MeCO，CF（3）CO，t-BuOCO）的C-糖苷可通过用活化的烯烃捕获异头基团以立体选择性方式获得。使用异头硒化物，在避免竞争性还原的条件下进行自由基的产生和捕获，并且该化学方法已用于合成O-苄基α-D-GalNAc的新型C-糖苷类似物。

  DOI：

  10.1021/ol006682c

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.