(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-methoxy-phosphoryl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 202644-72-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-methoxy-phosphoryl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 202644-72-2
• 化学式: C₃₆H₄₉N₄O₂₂P
• 分子量: 920.772
• InChiKey: JMOWOZUSJUQFOL-KWMNIDJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.66
• 重原子数：
  63.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  331.18
• 氢给体数：
  2.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-methoxy-phosphoryl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 、 Amberlite IR 120 、 sodium methylate 、 苯硫酚 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of phosphonate analogues of CMP-Neu5Ac determination of α(2–6)-sialyltransferase inhibition

  摘要：

  Treatment of sialyl phosphites with TMSOTf as catalyst affords alpha-and beta-sialyl phosphonates. This phospshite/phosphonate-exchange reaction was employed for the synthesis of sialylphosphonate dialkyl esters 5a alpha-5c alpha and 58 beta-5c beta. Monodemethylation of 5c alpha and 5c beta, linkage to 5'-O-unprotected cytidine derivative 7, and then deprotection furnished the phosphonate analogue 2 beta of CMP-Neu5Ac and the corresponding alpha-isomer 2 alpha, respectively. Their structures could be assigned and inhibition of alpha(2-6)-sialyltransferase was determined. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10625-6
• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 、 偶氮二甲酸二异丙酯 、 苯硫酚 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{[(2R,3R,4R,5R)-3,4-diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-methoxy-phosphoryl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of phosphonate analogues of CMP-Neu5Ac determination of α(2–6)-sialyltransferase inhibition

  摘要：

  Treatment of sialyl phosphites with TMSOTf as catalyst affords alpha-and beta-sialyl phosphonates. This phospshite/phosphonate-exchange reaction was employed for the synthesis of sialylphosphonate dialkyl esters 5a alpha-5c alpha and 58 beta-5c beta. Monodemethylation of 5c alpha and 5c beta, linkage to 5'-O-unprotected cytidine derivative 7, and then deprotection furnished the phosphonate analogue 2 beta of CMP-Neu5Ac and the corresponding alpha-isomer 2 alpha, respectively. Their structures could be assigned and inhibition of alpha(2-6)-sialyltransferase was determined. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10625-6