3-deoxy-3-(thymin-1'-yl)-2,5-anhydro-D-mannitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-(thymin-1'-yl)-2,5-anhydro-D-mannitol
• 英文别名: 2,5-Anhydro-3-deoxy-3-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-D-mannitol；1-[(2S,3S,4S,5R)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: DIIAHMIWVVBGBN-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-脱水-d-甘露糖 在 吡啶 、 sodium tetrahydroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.0h， 生成 3-deoxy-3-(thymin-1'-yl)-2,5-anhydro-D-mannitol
  参考文献：
  名称：

  Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-d-mannitol: a novel class of hydroxymethyl-branched isonucleosides

  摘要：

  A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol 6(a-d) has been achieved, using the deamination of 2-amino-2-deoxy-D-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro-D-mannitol 9 was investigated, and the key epoxide intermediate 13 was obtained in good yield via an intramolecular Mitsunobu reaction. The process of opening of epoxide 13 by nucleobases appeared to be regioselective. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00246-9

文献信息

• Fructose analogs and their combinations as anti-cancer agents
  申请人：Jia Wei

  公开号：US10441564B2

  公开（公告）日：2019-10-15

  The present invention provides a fructose analogue and a composition thereof which can be used for cancer treatment, has a targeting effect and has little effect on normal cells, particularly when used in the treatment of acute myeloid leukemia (‘AML’) and pancreatic cancer and other types of cancer having similar metabolic characteristics. In the present invention, the fructose analog is selected from the group consisting of 2,5-anhydro-D-mannitol and the 2,5-anhydro-D-mannitol derivative substituted at the 1-position or 6-position by an amino group, an alkyl group or an aryl group, anhydro-D-mannitol tetraacetate and 2,5-anhydroglucitol and the like. The fructose analogs of the present invention can be used to prepare and treat cancer drugs and can be prepared as injectable preparations or oral preparations. The fructose analogues of the present invention can be used in combination with conventional anticancer drugs when used in the preparation of a medicament for the treatment of cancer. The fructose analogs of the present invention can be used in combination with glucose analogues in the treatment of cancer or organ fibrosis.

  本发明提供了一种果糖类似物及其组合物，可用于癌症治疗，具有靶向作用，对正常细胞影响小，尤其是用于治疗急性髓性白血病（"AML"）和胰腺癌以及具有类似代谢特征的其他类型癌症时。在本发明中，果糖类似物选自 2,5-脱水-D-甘露醇和在 1 位或 6 位被氨基、烷基或芳基取代的 2,5-脱水-D-甘露醇衍生物、脱水-D-甘露醇四乙酸酯和 2,5-脱水葡萄糖醇等组成的组。本发明的果糖类似物可用于制备和治疗癌症药物，可以制备成注射制剂或口服制剂。在制备治疗癌症的药物时，本发明的果糖类似物可与常规抗癌药物联合使用。本发明的果糖类似物可与葡萄糖类似物联合用于治疗癌症或器官纤维化。
• Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-d-mannitol: a novel class of hydroxymethyl-branched isonucleosides
  作者：Z Lei、J.M Min、L.H Zhang

  DOI：10.1016/s0957-4166(00)00246-9

  日期：2000.7

  A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol 6(a-d) has been achieved, using the deamination of 2-amino-2-deoxy-D-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro-D-mannitol 9 was investigated, and the key epoxide intermediate 13 was obtained in good yield via an intramolecular Mitsunobu reaction. The process of opening of epoxide 13 by nucleobases appeared to be regioselective. (C) 2000 Elsevier Science Ltd. All rights reserved.