(1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-benzyl-N1-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate | 696629-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-benzyl-N1-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate
• 英文别名: (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N³-benzyl-N¹-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate
• CAS: 696629-11-5
• 化学式: C₃₃H₄₄N₂O₁₀
• 分子量: 628.72
• InChiKey: NSLOMJMUZWCPJG-RYEBQZEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  123.25
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-benzyl-N1-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate 在 4 A molecular sieve 、 四丁基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以95%的产率得到(1'R,2'R,3'S,4'S,5'R,6S) N³-benzyl-N¹-(3,4-dimethoxyphenylmethyl)-5,6-dihydro-6-(1',2':3',4'-di-O-isopropylidene-1',2',3',4'-tetrahydro-1',5'-pyranos-5'-yl)-pyrimidin-2,4-dione
  参考文献：
  名称：

  Diastereoselective Synthesis of Galactopyranosyl Amino Esters and Their Transformation into C‐Nucleosides

  摘要：

  Galactopyranosylated olefinic ester (4) on conjugate addition of amines yielded stereoselectively galactopyranosylated amino esters (5-18) in fair to good yield. The selected amino esters (5, 6, 13, and 15-17) on reaction with isocyanates resulted in ureido galactopyranosyl amino esters (19-24) in very good yields. Lactamization of compounds 19-24 with DBU, 4 Angstrom MS, and tetrabutylammonium bromide in refluxing toluene gave respective C-galactopyranosyl dihydropyrimidine-2,4-diones (25-30) in respectable yields.

  DOI：

  10.1081/car-120030140
• 作为产物：
  描述：

  ethyl (methyl 1,2:3,4-di-O-isopropylidene-6-amino-6,7-dideoxy-L-glycero-α-D-galacto-octopyranoside)uronate 在 sodium cyanoborohydride 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (1R,2R,3S,4S,5R,6S) ethyl [6,7-dideoxy-6-{N3-benzyl-N1-(3,4-dimethoxyphenyl methyl)-(1-ureidyl)}-1,2:3,4-di-O-isopropylidene-tetrahydro-1,5-octopyranos-5-yl]-uronate
  参考文献：
  名称：

  Diastereoselective Synthesis of Galactopyranosyl Amino Esters and Their Transformation into C‐Nucleosides

  摘要：

  Galactopyranosylated olefinic ester (4) on conjugate addition of amines yielded stereoselectively galactopyranosylated amino esters (5-18) in fair to good yield. The selected amino esters (5, 6, 13, and 15-17) on reaction with isocyanates resulted in ureido galactopyranosyl amino esters (19-24) in very good yields. Lactamization of compounds 19-24 with DBU, 4 Angstrom MS, and tetrabutylammonium bromide in refluxing toluene gave respective C-galactopyranosyl dihydropyrimidine-2,4-diones (25-30) in respectable yields.

  DOI：

  10.1081/car-120030140