1-C-acetylmethyl 5-azido-2,3-di-O-benzyl-5-deoxy-α-D-ribofuranoside | 872454-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-C-acetylmethyl 5-azido-2,3-di-O-benzyl-5-deoxy-α-D-ribofuranoside
• 英文别名: 1-[(2R,3S,4R,5R)-5-(azidomethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]propan-2-one
• CAS: 872454-78-9
• 化学式: C₂₂H₂₅N₃O₄
• 分子量: 395.458
• InChiKey: AGNJZPWCGFFVHC-YUMYIRISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-C-acetylmethyl 5-azido-2,3-di-O-benzyl-5-deoxy-α-D-ribofuranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 1-((2R,3S,4R,5R)-5-Aminomethyl-3,4-bis-benzyloxy-tetrahydro-furan-2-yl)-propan-2-one
  参考文献：
  名称：

  1-C-(2′-Oxoalkyl) glycosides as latent α,β-unsaturated conjugates. Synthesis of aza-C-glycosides by an intramolecular hetero-Michael addition

  摘要：

  1-C-(2'-Oxoalkyl)-5-azido-5-deoxy-glycofuranosides were used as latent substrates for intramolecular hetero-Michael addition. Reduction of the azido groups by catalytic hydrogenation followed by base treatment produced 2-ester and 2'-ketone aza-C-glycopyranosides. The conjugation addition was stereoselective in favor of aza-C-glycosides with equatorial Substitutions at the pseudo anomeric center. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.037
• 作为产物：
  描述：

  Methanesulfonic acid (2R,3R,4S)-5-allyl-3,4-bis-benzyloxy-tetrahydro-furan-2-ylmethyl ester 在 sodium azide 、 jones reagent 、 mercury(II) diacetate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 1-C-acetylmethyl 5-azido-2,3-di-O-benzyl-5-deoxy-α-D-ribofuranoside
  参考文献：
  名称：

  1-C-(2′-Oxoalkyl) glycosides as latent α,β-unsaturated conjugates. Synthesis of aza-C-glycosides by an intramolecular hetero-Michael addition

  摘要：

  1-C-(2'-Oxoalkyl)-5-azido-5-deoxy-glycofuranosides were used as latent substrates for intramolecular hetero-Michael addition. Reduction of the azido groups by catalytic hydrogenation followed by base treatment produced 2-ester and 2'-ketone aza-C-glycopyranosides. The conjugation addition was stereoselective in favor of aza-C-glycosides with equatorial Substitutions at the pseudo anomeric center. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.037