2,5-anhydro-4,5-di-O-benzoyl-D-glucitol | 75499-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol
• 英文别名: 2,5-anhydro-4,6-di-O-benzoyl-D-glucitol；2,5-Anhydro-4,6-di-O-benzoyl-D-glucitol；[(2R,3S,4R,5S)-3-benzoyloxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl benzoate
• CAS: 75499-83-1
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: SSDDKLJPMGOGSJ-BSDSXHPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-4,5-di-O-benzoyl-D-glucitol 在 四溴化碳 、 sodium methylate 、 三苯基膦 、 红铝 作用下， 以 吡啶 、 甲醇 、 氯仿 、 苯 为溶剂， 反应 118.0h， 生成 2,5-anhydro-6-bromo-1,4-dideoxy-D-ribo-hexitol
  参考文献：
  名称：

  Mubarak, Azeez M.; Brown, Daniel M., Journal of the Chemical Society. Perkin transactions I, 1982, p. 809 - 814

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-anhydro-1,3-O-isopropylidene-D-glucitol 在 硫酸 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol
  参考文献：
  名称：

  Synthesis of Homo-C-D4T and Homo-C-Thymidine

  摘要：

  beta-C-Vinyl glycoside of D-arabinofuranose was converted to the beta-C-hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2',3'-dideoxy-2',3'-didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.

  DOI：

  10.1080/07328319708006130

文献信息

• D-Arbinose-Based Synthesis of homo-<i>C</i>-d4T and homo-<i>C</i>-thymidine
  作者：Bogdan Doboszewski

  DOI：10.1080/15257770903306518

  日期：2009.10.28

  2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. D-Arbinose-Based Synthesis of homo-C-d4T and homo-C-thymidineAll authorsBogdan Doboszewskihttps://doi.org/10.1080/15257770903306518 Published online:20 October 2009

  使2,3,5-Tri- O-苄基-D-阿拉伯呋喃糖基卤化物（氯化物，溴化物）与AllMgBr，MeMgBr和VinMgBr反应，以提供C-糖基产物的异头混合物。讨论了影响β/α比的因素。将α，β- C-乙烯基衍生物转化为1-脱氧-1- C-羟甲基-β-和-α-D-阿拉伯呋喃糖酶（分别为2,5-脱水-D-葡萄糖醇和-甘露醇），可在分离后分离异丙基化步骤。2,5-脱水-1,3- O-异亚丙基-D-葡萄糖醇被转化为2,5-脱水-6- O-三苯甲基-D-赤型-hex-3,4-烯醇和2,5-脱水- 4,6-二-O-苯甲酰基-3-脱氧-D-核糖-己糖醇，在Mitsunobu条件下与N-3-苯甲酰胸腺嘧啶偶联，以提供两个在糖基团和胸腺嘧啶之间插入-CH 2-的核苷类似物。 的d-Arbinose基于合成均聚物Ç -d4T和均聚Ç -胸苷所有作者Bogdan Doboszewski https://doi
• A simple, stereospecific synthesis of (+)-muscarine
  作者：Azeez M. Mubarak、Daniel M. Brown

  DOI：10.1016/s0040-4039(00)93174-5

  日期：1980.1

  A high-yielding stereospecific synthesis of the toxic principle (+)-muscarine from -mannitol via 2,5-anhydro--glucitol is described.

  描述了由-甘露糖醇经由2，5-脱水-葡萄糖醇的毒性原理（+）-毒蕈碱的高产率立体定向合成。
• A synthesis of β-2′-deoxyshowdomycin
  作者：Azeez M. Mubarak、Daniel M. Brown

  DOI：10.1016/s0040-4039(01)92522-5

  日期：1981.1

  A stereospecific synthesis of the 2′-deoxy analogue of showdomycin, 2-(2′-deoxy-β-D-ribofuranosyl)-maleimide, from 2,5-anhydro-D-glucitol is described.

  描述了从2，5-脱水-D-葡萄糖醇立体合成秀木霉素的2'-脱氧类似物2-（2'-脱氧-β-D-呋喃呋喃糖基）-马来酰亚胺。
• 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 Homo-C-D4T and Homo-C-Thymidine
  作者：Bogdan Doboszewski

  DOI：10.1080/07328319708006130

  日期：1997.7

  beta-C-Vinyl glycoside of D-arabinofuranose was converted to the beta-C-hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2',3'-dideoxy-2',3'-didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.