methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-xylo-hexofuranosid-5-ulose | 1449769-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-xylo-hexofuranosid-5-ulose
• 英文别名: N-[(2R,3R,4R,5S)-2-methoxy-4-phenylmethoxy-5-(2-phenylmethoxyacetyl)oxolan-3-yl]acetamide
• CAS: 1449769-63-4
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: YLVFLPOZXDJQSV-SSGKUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-xylo-hexofuranosid-5-ulose 、 亚磷酸二甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 2.0h， 以69%的产率得到methyl (5R)-2-acetamido-3,6-di-O-benzyl-2-deoxy-5-C-dimethoxyphosphoryl-β-D-xylo-hexofuranoside
  参考文献：
  名称：

  Synthesis of 2-Acetamido-2,5-dideoxy-5-phosphoryl-D-glucopyranose Derivatives: New Phospha-sugar Analogs of N-Acetyl-D-glucosamine

  摘要：

  Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).

  DOI：

  10.3987/com-12-s(n)69
• 作为产物：
  描述：

  N-乙酰氨基葡萄糖 在 盐酸 、 iron(III) chloride 、 草酰氯 、 二正丁基氧化锡 、 溶剂黄146 、 二甲基亚砜 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 70.5h， 生成 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-xylo-hexofuranosid-5-ulose
  参考文献：
  名称：

  Synthesis of 2-Acetamido-2,5-dideoxy-5-phosphoryl-D-glucopyranose Derivatives: New Phospha-sugar Analogs of N-Acetyl-D-glucosamine

  摘要：

  Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).

  DOI：

  10.3987/com-12-s(n)69

文献信息

• Synthesis of 2-Acetamido-2,5-dideoxy-5-phosphoryl-D-glucopyranose Derivatives: New Phospha-sugar Analogs of N-Acetyl-D-glucosamine
  作者：Tadashi Hanaya、Masahiro Kawaguchi、Masakazu Sumi、Kazuo Makino、Keiko Tsukada、Hiroshi Yamamoto

  DOI：10.3987/com-12-s(n)69

  日期：——

  Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).