Acetic acid (1S,2R)-2,3-diacetoxy-1-((2R,3R,4S)-4-acetoxy-3-acetylamino-6-formyl-3,4-dihydro-2H-pyran-2-yl)-propyl ester | 211231-63-9

• 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: Acetic acid (1S,2R)-2,3-diacetoxy-1-((2R,3R,4S)-4-acetoxy-3-acetylamino-6-formyl-3,4-dihydro-2H-pyran-2-yl)-propyl ester
• CAS: 211231-63-9
• 化学式: C₁₉H₂₅NO₁₁
• 分子量: 443.408
• InChiKey: PVHQNZPUMGWGTH-UURKPOQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  160.6
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R)-2,3-diacetoxy-1-((2R,3R,4S)-4-acetoxy-3-acetylamino-6-formyl-3,4-dihydro-2H-pyran-2-yl)-propyl ester 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Acetic acid (R)-[(4S,5R,6R)-4-acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5,6-dihydro-4H-pyran-2-yl]-(bis-benzyloxy-phosphoryl)-methyl ester
  参考文献：
  名称：

  New Potent Sialyltransferase Inhibitors—Synthesis of Donor and of Transition-State Analogues of Sialyl Donor CMP-Neu5Ac

  摘要：

  Enzymatic sialyl transfer with CMP-Neu5Ac as donor can be inhibited by CDP. Therefore phosphonates 1a,b, 2 and 3 were synthesized as substrate analogues. With alpha(2-6)-sialyltransferase from rat liver (EC2.4.99.1) only moderate inhibition was found for these compounds. In order to obtain transition-state analogues of CMP-Neu5Ac different linkages between 2,3-dehydro-N-acetylneuraminol and CMP were generated, yielding 4, (R)-5 and (R)-6. Compound (R)-6, in which the CMP residue is attached to C-1 of 2,3-dehydro-N-acetylneuramin-1-yl phosphonate, exhibited excellent alpha(2-6)-sialyltransferase inhibition in the nanomolar range (K-i=350 nM), resulting in a 130-fold higher affinity for the enzyme than CMP-Neu5Ac (K-M = 46 mu M).

  DOI：

  10.1002/(sici)1521-3765(19980615)4:6<1106::aid-chem1106>3.0.co;2-7
• 作为产物：
  描述：

  在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以82%的产率得到Acetic acid (1S,2R)-2,3-diacetoxy-1-((2R,3R,4S)-4-acetoxy-3-acetylamino-6-formyl-3,4-dihydro-2H-pyran-2-yl)-propyl ester
  参考文献：
  名称：

  New Potent Sialyltransferase Inhibitors—Synthesis of Donor and of Transition-State Analogues of Sialyl Donor CMP-Neu5Ac

  摘要：

  Enzymatic sialyl transfer with CMP-Neu5Ac as donor can be inhibited by CDP. Therefore phosphonates 1a,b, 2 and 3 were synthesized as substrate analogues. With alpha(2-6)-sialyltransferase from rat liver (EC2.4.99.1) only moderate inhibition was found for these compounds. In order to obtain transition-state analogues of CMP-Neu5Ac different linkages between 2,3-dehydro-N-acetylneuraminol and CMP were generated, yielding 4, (R)-5 and (R)-6. Compound (R)-6, in which the CMP residue is attached to C-1 of 2,3-dehydro-N-acetylneuramin-1-yl phosphonate, exhibited excellent alpha(2-6)-sialyltransferase inhibition in the nanomolar range (K-i=350 nM), resulting in a 130-fold higher affinity for the enzyme than CMP-Neu5Ac (K-M = 46 mu M).

  DOI：

  10.1002/(sici)1521-3765(19980615)4:6<1106::aid-chem1106>3.0.co;2-7