1,2,3,6-tetra-O-acetyl-4-O-[3'-O-{2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl}-2,4-di-O-acetyl-β-D-galactopyranosyl]-α-D-mannopyranose | 688317-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,6-tetra-O-acetyl-4-O-[3'-O-{2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl}-2,4-di-O-acetyl-β-D-galactopyranosyl]-α-D-mannopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 688317-25-1
• 化学式: C₃₈H₅₂O₂₆
• 分子量: 924.815
• InChiKey: JRZBAHKYTPQJCV-AGHASXGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  64
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  329
• 氢给体数：
  1
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-[3'-O-{2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl}-2,4-di-O-acetyl-β-D-galactopyranosyl]-α-D-mannopyranose 、 1,2,3,6-tetra-O-acetyl-4-O-[3'-O-{2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl}-2,4-di-O-acetyl-6'-O-(tert0butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranosyl H-phosphonate triethylammonium salt 在 三甲基乙酰氯 、 碘 作用下， 以 吡啶 、 水 为溶剂， 反应 1.5h， 以79%的产率得到[(2R,3S,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl] [(2R,3S,4S,5R,6S)-3,5-diacetyloxy-4-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5S,6R)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl phosphate;triethylazanium
  参考文献：
  名称：

  A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite

  摘要：

  A novel approach for the iterative synthesis of the antigenic branched phosphoglycan of the protozoan parasite Leishmania major is presented that exploits remarkable dual selectivity in the functionalization of D-lactal, providing flexibility to extend the PG chain either towards the reducing or nonreducing end. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.155
• 作为产物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-[3'-O-{2,3,4,6-tetra-O-acetyl-β-galactopyranosyl}-2,4-di-O-acetyl-6'-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以85%的产率得到1,2,3,6-tetra-O-acetyl-4-O-[3'-O-{2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl}-2,4-di-O-acetyl-β-D-galactopyranosyl]-α-D-mannopyranose
  参考文献：
  名称：

  A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite

  摘要：

  A novel approach for the iterative synthesis of the antigenic branched phosphoglycan of the protozoan parasite Leishmania major is presented that exploits remarkable dual selectivity in the functionalization of D-lactal, providing flexibility to extend the PG chain either towards the reducing or nonreducing end. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.155