(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(dimethoxy-phosphoryl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 176097-01-1

• 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: (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(dimethoxy-phosphoryl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[dimethoxy(oxido)phosphaniumyl]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 176097-01-1
• 化学式: C₂₂H₃₄NO₁₅P
• 分子量: 583.483
• InChiKey: HZWQBZOUVMGKPS-ZJGVECAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  211
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(dimethoxy-phosphoryl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 Amberlite IR 120 、 sodium methylate 、 苯硫酚 、 三苯基膦 作用下， 以 四氢呋喃 、 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：

  4,5,7,8,9-pentaacetyl-2-(diethylphospho)-α,β-neuraminic acid methyl ester 在 二甲基三甲硅基膦酸酯 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(dimethoxy-phosphoryl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  具有糖基膦酸酯结构的新型CMP-NeuNAc类似物的合成

  摘要：

  使用TMSOTf作为催化剂，通过亚磷酸三甲基甲硅烷基亚磷酸酯的亚磷酸三甲硅烷基酯的亲核取代，合成了唾液酸磷酸酯，并使用Mitsunobu缩合反应将其转化为CMP-NeuNAc类似物2。

  DOI：

  10.1016/0040-4039(96)00069-x

文献信息

• Synthesis of novel CMP-NeuNAc analogues having a glycosyl phosphonate structure
  作者：Masakazu Imamura、Hironobu Hashimoto

  DOI：10.1016/0040-4039(96)00069-x

  日期：1996.2

  Sialyl phosphonate was synthesized by nucleophilic substitution of sialyl phosphite with dimethyl trimethylsilyl phosphite using TMSOTf as a catalyst and converted to CMP-NeuNAc analogue 2 using Mitsunobu condensation.

  使用TMSOTf作为催化剂，通过亚磷酸三甲基甲硅烷基亚磷酸酯的亚磷酸三甲硅烷基酯的亲核取代，合成了唾液酸磷酸酯，并使用Mitsunobu缩合反应将其转化为CMP-NeuNAc类似物2。
• Synthesis of phosphonate analogues of CMP-Neu5Ac determination of α(2–6)-sialyltransferase inhibition
  作者：Bernd Müller、Thomas J. Martin、Christoph Schaub、Richard R. Schmidt

  DOI：10.1016/s0040-4039(97)10625-6

  日期：1998.2

  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.