(4R,5R)-5-hydroxy-1-(metyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-(D-arabino-tetritol-1-yl)imidazolidine-2-thione | 250265-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-5-hydroxy-1-(metyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-(D-arabino-tetritol-1-yl)imidazolidine-2-thione
• 英文别名: Ltwwrjlhqivknq-zpyorwkpsa-；(4R,5R)-1-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]-5-hydroxy-4-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]imidazolidine-2-thione
• CAS: 250265-37-3
• 化学式: C₁₄H₂₆N₂O₁₀S
• 分子量: 414.434
• InChiKey: LTWWRJLHQIVKNQ-ZPYORWKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  228
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-hydroxy-1-(metyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-(D-arabino-tetritol-1-yl)imidazolidine-2-thione 在 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 5.5h， 生成 1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-(D-arabino-tetritol-1-yl)-4-imidazoline-2-thione
  参考文献：
  名称：

  Stereoselective synthesis of imidazolidine, imidazoline and imidazole C- and N-pseudonucleosides

  摘要：

  Methyl 2-deoxy-2-isothiocyanato-alpha-D-glucopyranoside 2, which exists in equilibrium with the corresponding 2,3-cyclic carbamate 1, reacts with D-glucosamine producing the pseudo-C and N-nucleoside of chiral imidazolidine-2-thione 3, in good yield and high stereoselectivity. Starting from 3, different pseudo-C- and N-nucleosides of imidazoline-2-thione 6-11, and of imidazole 12 and 13 are obtained. Conformational aspects of some of the prepared compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00314-6
• 作为产物：
  描述：

  2-deoxy-2-amino glucose 、 硫光气 、 Methyl 2-benzamido-2-deoxy-α-D-glucopyranoside 在 sodium hydroxide 、 二氧化碳 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 34.17h， 以72%的产率得到(4R,5R)-5-hydroxy-1-(metyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-(D-arabino-tetritol-1-yl)imidazolidine-2-thione
  参考文献：
  名称：

  Stereoselective synthesis of imidazolidine, imidazoline and imidazole C- and N-pseudonucleosides

  摘要：

  Methyl 2-deoxy-2-isothiocyanato-alpha-D-glucopyranoside 2, which exists in equilibrium with the corresponding 2,3-cyclic carbamate 1, reacts with D-glucosamine producing the pseudo-C and N-nucleoside of chiral imidazolidine-2-thione 3, in good yield and high stereoselectivity. Starting from 3, different pseudo-C- and N-nucleosides of imidazoline-2-thione 6-11, and of imidazole 12 and 13 are obtained. Conformational aspects of some of the prepared compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00314-6