Phenyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside | 161822-73-7

• 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-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside
• 英文别名: N-[(2R,3R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylselanyloxan-3-yl]acetamide
• CAS: 161822-73-7
• 化学式: C₃₅H₃₇NO₅Se
• 分子量: 630.642
• InChiKey: IKNKORKYJPLODW-CKQPALCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Phenyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 在 mercury(II) trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以91%的产率得到2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose
  参考文献：
  名称：

  Convenient Preparation of Perbenzylated 2-Azido and 2-N-Acetylamino-2-Deoxy-d-Hexono-1,5-Lactones by Oxidation of the Corresponding Lactols

  摘要：

  2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).

  DOI：

  10.1080/07328309608005438
• 作为产物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 在 吡啶 、 1,2-丙二硫醇 、 叠氮基三甲基硅烷 、 四丁基氟化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 Phenyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00105a051

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.
• Convenient Preparation of Perbenzylated 2-Azido and 2-<i>N</i>-Acetylamino-2-Deoxy-<scp>d</scp>-Hexono-1,5-Lactones by Oxidation of the Corresponding Lactols
  作者：Ebtissam Ayadi、Stanislas Czernecki、Juan Xie

  DOI：10.1080/07328309608005438

  日期：1996.2

  2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).