dibenzyl [methyl (4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)ulonate] phosphite | 866332-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzyl [methyl (4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)ulonate] phosphite
• 英文别名: methyl (2R,4S,5R,6R)-4-acetyloxy-2-bis(phenylmethoxy)phosphanyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxane-2-carboxylate
• CAS: 866332-35-6
• 化学式: C₃₄H₃₉F₃NO₁₅P
• 分子量: 789.65
• InChiKey: WLVKXTQZFPBFRZ-JYBVLBACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  dibenzyl [methyl (4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)ulonate] phosphite 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 生成 methyl 4,7,8-tri-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-9-O-(methyl-5-trifluoroacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosidonate
  参考文献：
  名称：

  N-Trifluoroacetyl Sialyl Phosphite Donors for the Synthesis of α(2 → 9) Oligosialic Acids

  摘要：

  A new method for the synthesis of alpha(2 -> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.

  DOI：

  10.1021/ol0515210
• 作为产物：
  描述：

  (2S,4S,5R,6R)-5-Amino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 四氮唑 、 N-溴代丁二酰亚胺(NBS) 、 水 、 三乙胺 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成 dibenzyl [methyl (4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)ulonate] phosphite
  参考文献：
  名称：

  N-Trifluoroacetyl Sialyl Phosphite Donors for the Synthesis of α(2 → 9) Oligosialic Acids

  摘要：

  A new method for the synthesis of alpha(2 -> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.

  DOI：

  10.1021/ol0515210