Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate | 353301-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate
• CAS: 353301-96-9
• 化学式: C₂₄H₃₂BrNO₁₀
• 分子量: 574.423
• InChiKey: DDDABRJPHGHMCS-YTIXMYJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  138.85
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.83h， 生成 Methyl 5-acetamido-4-O-benzyl-3,5-dideoxy-8,9-O-isopropylidene-3-phenylthio-β-D-erythro-L-gluco-2-nonulopyranosonate-diethylphosphite
  参考文献：
  名称：

  Synthesis of Ganglioside GD3 and its Comparison with Bovine GD3 with Regard to Oligodendrocyte Apoptosis Mitochondrial Damage

  摘要：

  2,3-Dehydroneuraminic acid derivative 5 was transformed in five efficient steps into sialyl donor 2, which has a phenylthio group on the beta-side of the 3-position for anchimeric assistance and a diethyl phosphite residue as leaving group at the anomeric carbon. The known GM3 intermediate 10 was transformed into the 4b,4c,8c-O-unprotected acceptor 3, which was then allowed to react with 2 by using TMSOTf as catalyst and acetonitrile as solvent to afford the desired tetrasaccharide 12, which has an alpha(2-8)-linkage between two neuraminic acid residues. Removal of the phenylthio group gave intermediate 13, which was transformed into O-tetraosyl trichloroacetimidate 16 as glycosyl donor. Application of the azidosphingosine glycosylation procedure furnished GD3 (1) in high overall yield. Comparison of synthetic GD3 with bovine-brain-derived GD3 showed that there were similar effects in GD3-triggered uncoupling of mitochondrial respiration and in induction of apoptosis in oligodendrocytes.

  DOI：

  10.1002/1521-3765(20010518)7:10<2178::aid-chem2178>3.0.co;2-e
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以1.85 g的产率得到Methyl 5-acetamido-4-O-benzyl-3-bromo-3,5-dideoxy-8,9-O-isopropylidene-β-D-erythro-L-manno-2-nonulopyranosonate
  参考文献：
  名称：

  Synthesis of Ganglioside GD3 and its Comparison with Bovine GD3 with Regard to Oligodendrocyte Apoptosis Mitochondrial Damage

  摘要：

  2,3-Dehydroneuraminic acid derivative 5 was transformed in five efficient steps into sialyl donor 2, which has a phenylthio group on the beta-side of the 3-position for anchimeric assistance and a diethyl phosphite residue as leaving group at the anomeric carbon. The known GM3 intermediate 10 was transformed into the 4b,4c,8c-O-unprotected acceptor 3, which was then allowed to react with 2 by using TMSOTf as catalyst and acetonitrile as solvent to afford the desired tetrasaccharide 12, which has an alpha(2-8)-linkage between two neuraminic acid residues. Removal of the phenylthio group gave intermediate 13, which was transformed into O-tetraosyl trichloroacetimidate 16 as glycosyl donor. Application of the azidosphingosine glycosylation procedure furnished GD3 (1) in high overall yield. Comparison of synthetic GD3 with bovine-brain-derived GD3 showed that there were similar effects in GD3-triggered uncoupling of mitochondrial respiration and in induction of apoptosis in oligodendrocytes.

  DOI：

  10.1002/1521-3765(20010518)7:10<2178::aid-chem2178>3.0.co;2-e