methyl (2-C-(2-oxa-2-phenylethyl)-5-N-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate | 1359855-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2-C-(2-oxa-2-phenylethyl)-5-N-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate
• 英文别名: methyl (2-C-(2-oxo-2-phenylethyl)-5-N-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate；methyl (3aR,4R,6S,7aS)-3-acetyl-2-oxo-6-phenacyl-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate
• CAS: 1359855-60-9
• 化学式: C₂₇H₃₁NO₁₃
• 分子量: 577.542
• InChiKey: SGNQBAIRSCAPQH-SADCBOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (2-C-(2-oxa-2-phenylethyl)-5-N-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.58h， 以85%的产率得到methyl (2-C-(2-oxo-2-phenylethyl)-5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate
  参考文献：
  名称：

  Stereoselective, Electrophilic α-C-Sialidation

  摘要：

  5-N-Acetyl-5-N,4-O-oxazolidinone protected alpha- and beta-sialyl phosphates react with allyltributylstannane and a variety of trimethylsilyl enol ethers to give alpha-sialyl C-glycosides in high yield and excellent selectivity. Elimination to give the 2,3-glycal is minimized by the presence of the oxazolidinone ring. The oxazolidinone ring can be subsequently cleaved under mild conditions at room temperature leaving in place the native acetamide group.

  DOI：

  10.1021/ol300255q
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 methyl (3aR,4R,6S,7aS)-3-acetyl-6-(4-methylphenyl)sulfanyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate 在 4,4'-二甲苯亚砜 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.75h， 以88%的产率得到methyl (2-C-(2-oxa-2-phenylethyl)-5-N-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate
  参考文献：
  名称：

  Highly efficient α-C-sialylation promoted by (p-Tol)2SO/Tf2O with N-acetyl-5-N,4-O-oxazolidione protected thiosialoside as donor

  摘要：

  基于(p-Tol)2SO/Tf2O预活化策略，通过N-乙酰基-5-N,4-O-恶唑烷酮保护的硫代唾液酸与各种三甲基硅基烯醇醚及烯丙基三甲基硅烷的偶联反应，实现了α-唾液酸型C-糖苷的实用、简便及高产率合成。对于具有大亲核性值（N = 4.4–9.0）的强π-亲核试剂，无论是硅醚烯醇、硅醚乙缩醛还是烯丙基三甲基硅烷作为亲电C-唾液酸化试剂，均能获得高产率和极佳的α-选择性。

  DOI：

  10.1039/c3ob40876k