4-methoxyphenyl 2-azido-3-O-benzoyl-2-deoxy-α-D-galactopyranoside | 1132966-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2-azido-3-O-benzoyl-2-deoxy-α-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-5-azido-3-hydroxy-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxan-4-yl] benzoate
• CAS: 1132966-57-4
• 化学式: C₂₀H₂₁N₃O₇
• 分子量: 415.403
• InChiKey: DEAYQIMZDMXYJE-NUABRCLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2-azido-3-O-benzoyl-2-deoxy-α-D-galactopyranoside 、 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4R,5R)-5-azido-6-oxo-1,3,4-tris(phenylmethoxy)hexan-2-yl]oxyoxan-2-yl]methyl acetate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 以315 mg的产率得到[(2S,4aR,6R,7R,8R,8aR)-7-azido-2-[(1R,2R,3R,4R)-1-azido-2,3,5-tris(phenylmethoxy)-4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentyl]-6-(4-methoxyphenoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
  参考文献：
  名称：

  Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus

  摘要：

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.006
• 作为产物：
  描述：

  4-methoxyphenyl 2-azido-3-O-benzoyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 高氯酸 、 silica gel 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 以85%的产率得到4-methoxyphenyl 2-azido-3-O-benzoyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus

  摘要：

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.006

文献信息

• Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus
  作者：Chinmoy Mukherjee、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2008.12.006

  日期：2008.12

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.