1,2,3-tri-O-acetyl-D-glucopyranose | 78962-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-tri-O-acetyl-D-glucopyranose
• 英文别名: [(3R,4S,5R,6R)-2,3-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• CAS: 78962-48-8
• 化学式: C₁₂H₁₈O₉
• 分子量: 306.27
• InChiKey: GNYSCNOUXJBUSG-OZRWLHRGSA-N

物化性质

• 沸点：
  421.4±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-D-glucopyranose 在 吡啶 、 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 臭氧 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-O-(2'-methanesulfonyloxyethyl)-1,2,3,6-tetra-O-acetyl-α,β,D-glucopyranose
  参考文献：
  名称：

  4-O-和6-O-（2'-碘乙基）-d-葡萄糖的合成

  摘要：

  摘要将1,2,3,6-四-O-乙酰基-d-吡喃葡萄糖进行O-烯丙基化，然后进行臭氧化/还原反应，得到4-羟乙基衍生物。还使用烷基化/还原序列从1,2：3,5-双（O-亚甲基）-α-d-葡糖呋喃糖开始在C-6处引入该羟乙基取代基。然后通过碘化然后脱保护将这些4-和6-O-羟乙基衍生物转化为标题化合物。值得注意的是，这些醚中的碳碘键具有特殊的稳定性，这是其在单光子发射计算机断层扫描医学成像（SPECT）中潜在使用的前提。

  DOI：

  10.1016/s0008-6215(98)00180-3
• 作为产物：
  描述：

  4,6-O-(苯基亚甲基)-D-吡喃葡萄糖三乙酸酯 在 palladium on activated charcoal 氢气 、 乙酰氯 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 1,2,3-tri-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  β-Acarbose. VII. Approaches Towards the Synthesis of Some N-Linked Carba-Oligosaccharides

  摘要：

  3,4-脱水-1,6-二脱氧-1,6-表硒-β-D-葡萄糖经环己基胺处理后，生成氨基二醇，随后转化为葡萄糖。 环己胺处理，得到氨基二醇，随后将其转化为环氨基甲酸酯。 环氨基甲酸酯。 供体。将相同的 3,4-anhydro 糖和 1,6-epithio 类似物 1-epivalienamine 衍生物处理后，可得到相应的仲胺 转化为类似的环氨基甲酸酯。表硫代 类似物作为糖基供体并不成功，未能糖基化碳水化合物醇。 碳水化合物醇。另一方面，表硒化合物似乎可以 但在其分离所需的条件下，产物会发生分解。 但在分离所需的条件下，产物发生了分解。

  DOI：

  10.1071/ch99030

文献信息

• Synthesis of azido-deoxy and amino-deoxy glycosides and glycosyl fluorides for screening of glycosidase libraries and assembly of substituted glycosides
  作者：Hong-Ming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2018.07.007

  日期：2018.9

  useful tools in the probing of biological systems as well as in the assembly of libraries of derivatives using click chemistry or simple amine coupling approaches. A collection of methylumbelliferyl glycosides of various azido- and amino-deoxy sugar derivatives of glucose, galactose and xylose was synthesised via azide displacement of the corresponding triflate derivatives and subsequent modification.

  叠氮化物和胺取代的糖在探测生物系统以及使用点击化学或简单的胺偶联方法组装衍生物库中可能是有用的工具。通过叠氮化物置换相应的三氟甲磺酸衍生物并随后进行修饰，合成了葡萄糖，半乳糖和木糖的各种叠氮基和氨基脱氧糖衍生物的甲基伞形糖苷苷。这些化合物将在高通量筛选中用作底物，以鉴定可加工此类修饰糖的糖苷酶。还合成了每种修饰糖的α-糖基氟衍生物，以用作衍生自筛选中鉴定的酶的糖合酶底物。
• WATER SOLUBLE PLATINUM COMPLEXES FOR TUMOR TREATMENT AND PROCESS OF PREPARING SAME
  申请人：GUDUI BIOPHARMA TECHNOLOGY INC.

  公开号：US20150051387A1

  公开（公告）日：2015-02-19

  Disclosed are water-soluble platinum complexes for tumor treatment and preparation method, said platinum complexes being shown as formula (I); The present platinum complexes exhibiting superior cytotoxicity and efficacy compare to the clinical drug oxaliplatin, the design strategy of the present platinum complexes is to enhance the solubility and stability favor its clinical use.

  本文披露了一种用于肿瘤治疗的水溶性铂配合物及其制备方法，所述铂配合物表示为式（I）；本文的铂配合物在细胞毒性和疗效方面优于临床药物奥沙利铂，本文的铂配合物设计策略是增强其溶解性和稳定性，有利于其临床应用。
• USE OF FLUORINE-CONTAINING WATER SOLUBLE PLATINUM COMPLEX IN PREPARING DRUGS FOR PREVENTION AND TREATMENT OF CANCERS
  申请人：GUDUI BIOPHARMA TECHNOLOGY INC.

  公开号：US20140349955A1

  公开（公告）日：2014-11-27

  Disclosed in the present invention is the use of a fluorine-containing in preparing drugs for the prevention and treatment of tumors, said platinum complex being shown as formula (I). Experiments have demonstrated that the present fluorine-containing water soluble platinum complex is highly water soluble and exhibiting superior cytotoxicity and efficacy compare to the clinical platinum drugs. Said complex alone or in combination with other chemotherapeutics is able to treat cancer in mammals, and in particular, humans, said cancers including lung cancer, colon cancer, head and neck cancer, prostate cancer, breast cancer, ovarian cancer, cervical cancer, leukemia, lymphoid cancer, skin cancer, pancreatic cancer, liver cancer, bladder cancer, esophageal cancer, gastric cancer, male genital cancer or bone cancer.

  本发明揭示了在制备预防和治疗肿瘤药物时使用含氟铂配合物，该铂配合物的化学式为（I）。实验证明，该含氟水溶性铂配合物具有高度的水溶性，与临床铂类药物相比，具有优越的细胞毒性和疗效。该配合物单独或与其他化疗药物联合使用，能够治疗哺乳动物，特别是人类的癌症，包括肺癌、结肠癌、头颈癌、前列腺癌、乳腺癌、卵巢癌、宫颈癌、白血病、淋巴癌、皮肤癌、胰腺癌、肝癌、膀胱癌、食管癌、胃癌、男性生殖器癌或骨癌。
• Involvement of the S-aglycon in the conformational preferences of thioglucosides
  作者：Carlos A. Sanhueza、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.tetasy.2008.01.003

  日期：2008.2

  The conformational preferences of two series of alkyl beta-D-thioglucopyranosides in solution were investigated by NMR and CD. The rotamer populations of the hydroxymethyl group were found to depend on the structural nature of the S-aglycon. The population of the gt rotamer increased and that of the gg rotamer decreased as the alkyl group attached to the S atom increased in size. These rotamer populations have a linear correlation with the Taft' steric parameters, the n(S)-sigma(C-O)* exo-anomeric interaction may express these rotational preferences. Comparative analysis of the hydroxymethyl populations between alkyl O- and S-glucosides revealed identical or slightly higher gt and smaller gg populations for the latter compounds. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of iodobenzylidene and iodoethylidene acetals of d-glucose
  作者：Marie-Dominique Desruet、Christophe Morin、Lionel Ogier

  DOI：10.1016/s0008-6215(97)00088-8

  日期：1997.6

  The synthesis of two iodinated acetals of D-glucose, analogues of D-glucose acetals which are known to interact with the glucose transport protein GLuT, is presented. The iodobenzylidene acetal was obtained by acetalation of 1,2,3-tri-O-acetyl-D-glucopyranose, whereas the iodoethylidene acetal was prepared from the corresponding prop-2-enylidene derivative by an ozonation/reduction sequence, followed by iodination of the resulting hydroxyethylidene derivative. (C) 1997 Elsevier Science Ltd.