Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside | 161822-70-4

• 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-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylselanyloxan-3-yl]acetamide
• CAS: 161822-70-4
• 化学式: C₃₅H₃₇NO₅Se
• 分子量: 630.642
• InChiKey: IKNKORKYJPLODW-ZQPTVKGJSA-N

物化性质

• 沸点：
  757.5±60.0 °C(predicted)

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-glucopyranoside 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 3 A molecular sieve 、 mercury(II) trifluoroacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖酸-1,5-内酯
  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：

  phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside 在 吡啶 、 1,3-丙二硫醇 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 生成 Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside
  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

文献信息

• 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%).