1-C-allyl 5-azido-5-deoxy-2,3,6-tri-O-benzyl-α-D-galactofuranoside | 872454-81-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-C-allyl 5-azido-5-deoxy-2,3,6-tri-O-benzyl-α-D-galactofuranoside
• 英文别名: (2S,3S,4S,5R)-2-[(1R)-1-azido-2-phenylmethoxyethyl]-3,4-bis(phenylmethoxy)-5-prop-2-enyloxolane
• CAS: 872454-81-4
• 化学式: C₃₀H₃₃N₃O₄
• 分子量: 499.61
• InChiKey: BXGLWUDKUUOJOG-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-C-allyl 5-azido-5-deoxy-2,3,6-tri-O-benzyl-α-D-galactofuranoside 在 palladium on activated charcoal jones reagent 、 mercury(II) diacetate 、 氢气 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 4.33h， 生成 1-[(2R,3S,4S,5S)-5-((R)-1-Amino-2-benzyloxy-ethyl)-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：

  (2R,3R,4S,5S,6R)-6-Allyl-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-ol 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-C-allyl 5-azido-5-deoxy-2,3,6-tri-O-benzyl-α-D-galactofuranoside
  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