methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate | 361192-69-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate
• CAS: 361192-69-0
• 化学式: C₄₉H₅₆F₆N₂O₂₂S
• 分子量: 1171.04
• InChiKey: XLOIZBVNOSSMNW-GXGUNLSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  80.0
• 可旋转键数：
  23.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  305.52
• 氢给体数：
  2.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  methyl 2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 、 methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以42%的产率得到methyl (2S,4S,5R,6R)-4-acetyloxy-6-[(1S,2R)-1-acetyloxy-2-[(2S,4S,5R,6R)-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-3-phenylmethoxypropyl]-2-[(2S,3R,4S,5S,6R)-5-hydroxy-2-[(2R,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-[(2,2,2-trifluoroacetyl)amino]oxane-2-carboxylate
  参考文献：
  名称：

  A Stereoselective Approach for the Synthesis of α-Sialosides

  摘要：

  A highly efficient synthesis of the human melanoma associated antigen GD(3) derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent alpha-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.

  DOI：

  10.1021/jo010345f
• 作为产物：
  描述：

  methyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 吡啶 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 74.08h， 生成 methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid]onate
  参考文献：
  名称：

  A Stereoselective Approach for the Synthesis of α-Sialosides

  摘要：

  A highly efficient synthesis of the human melanoma associated antigen GD(3) derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent alpha-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.

  DOI：

  10.1021/jo010345f