(S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid (3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester | 196805-93-3

• 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: (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid (3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
• 英文别名: [(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoate
• CAS: 196805-93-3
• 化学式: C₂₇H₃₅N₃O₁₀
• 分子量: 561.589
• InChiKey: YYVBMDBTBAHKGO-OMTGHCCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid (3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 以 水 为溶剂， 反应 1.0h， 以94%的产率得到5'-O-(O-benzyl-L-seryl)-uridine trifluoroacetate
  参考文献：
  名称：

  Synthese von 5?-O-Aminos�urederivaten des Uridins als potentielle Inhibitoren derUDP-Glukuronosyl-Transferase

  摘要：

  In an attempt to develop potential inhibitors of UDP-glucuronosyltransferase, some 5'-O-amino acid derivatives of uridine were synthesized. N-protected L-amino acids were coupled at the 5'-O-position of 2',3'-O-isopropylideneuridine by esterification employing the method of symmetrical anhydrides in presence of 4-dimethylaminopyridine. 5'-O-(N-benzyloxycarbonyl-O-tert.butyl-L-threonyl)-2',3'-O-isopropylideneuridine (1), 5'-O-(N-tert.butyloxycarbonyl-O-benzyl-L-seryl)-2',3'-O-isopropylideneuridine (2), 5'-O-(N-tert.butyloxycarbonyl-L-leucyl)-2',3'-O-isopropylideneuridine (3), and 5'-O-(N-tert.butyloxycarbonyl-L-valyl)-2 (4) were obtained in good yield after column chromatography on silica gel. The treatment of 2 with TFA/CH2Cl2 (6:1) at room temperature for 30 min led to a selective removal of the Boc group without deblocking of the 2',3'-O-isopropylidene group of uridine. Treatment of 2 with TFA/H2O (5:1) at room temperature for Ih, however, released both Boc and 7/,3'-O-isopropylidene groups. The Z group of 1 was deprotected by catalytic hydrogenolysis over 10% Pd/C/ammonium formate.

  DOI：

  10.1007/bf00807604
• 作为产物：
  描述：

  N-BOC-O-苄基-L-丝氨酸 、 2’,3’邻异亚丙基尿苷 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid (3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  Synthese von 5?-O-Aminos�urederivaten des Uridins als potentielle Inhibitoren derUDP-Glukuronosyl-Transferase

  摘要：

  In an attempt to develop potential inhibitors of UDP-glucuronosyltransferase, some 5'-O-amino acid derivatives of uridine were synthesized. N-protected L-amino acids were coupled at the 5'-O-position of 2',3'-O-isopropylideneuridine by esterification employing the method of symmetrical anhydrides in presence of 4-dimethylaminopyridine. 5'-O-(N-benzyloxycarbonyl-O-tert.butyl-L-threonyl)-2',3'-O-isopropylideneuridine (1), 5'-O-(N-tert.butyloxycarbonyl-O-benzyl-L-seryl)-2',3'-O-isopropylideneuridine (2), 5'-O-(N-tert.butyloxycarbonyl-L-leucyl)-2',3'-O-isopropylideneuridine (3), and 5'-O-(N-tert.butyloxycarbonyl-L-valyl)-2 (4) were obtained in good yield after column chromatography on silica gel. The treatment of 2 with TFA/CH2Cl2 (6:1) at room temperature for 30 min led to a selective removal of the Boc group without deblocking of the 2',3'-O-isopropylidene group of uridine. Treatment of 2 with TFA/H2O (5:1) at room temperature for Ih, however, released both Boc and 7/,3'-O-isopropylidene groups. The Z group of 1 was deprotected by catalytic hydrogenolysis over 10% Pd/C/ammonium formate.

  DOI：

  10.1007/bf00807604