(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 119054-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 119054-35-2
• 化学式: C₂₆H₃₄N₂O₁₇
• 分子量: 646.559
• InChiKey: OJJQNJLYGVKBQY-HCKWTDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.87
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  242.74
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  D-mannosamine hydrochloride 、 (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 三乙胺 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 68.0h， 以30.5 mg的产率得到(2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-[((3S,4R,5S,6R)-2,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl)-methoxy]-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Neu5Acα(2→5)Neu5Gc:  The Building Block of Oligo/Poly(→5-O_glycolylNeu5Gcα2→) Chains in Sea Urchin Egg Cell Surface Glycoprotein

  摘要：

  The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.

  DOI：

  10.1021/jo025988p
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 methyl [2-(2'-oxido-2'-oxoethyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以92%的产率得到(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(2,5-dioxo-pyrrolidin-1-yloxycarbonylmethoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Neu5Acα(2→5)Neu5Gc:  The Building Block of Oligo/Poly(→5-O_glycolylNeu5Gcα2→) Chains in Sea Urchin Egg Cell Surface Glycoprotein

  摘要：

  The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.

  DOI：

  10.1021/jo025988p