1-C-acetylmethyl 5-azido-5-deoxy-2,3,6-tri-O-benzyl-α-D-galactofuranoside | 872454-82-5

• 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-5-deoxy-2,3,6-tri-O-benzyl-α-D-galactofuranoside
• CAS: 872454-82-5
• 化学式: C₃₀H₃₃N₃O₅
• 分子量: 515.609
• InChiKey: VIHNXTCQBHCFKH-ZNOUKXQUSA-N

反应信息

• 作为反应物：
  描述：

  1-C-acetylmethyl 5-azido-5-deoxy-2,3,6-tri-O-benzyl-α-D-galactofuranoside 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,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 、 jones reagent 、 mercury(II) diacetate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 9.0h， 生成 1-C-acetylmethyl 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