(1S,2R,3R,5S)-2,3,6-三羟基-4,8-二氧杂双环[3.3.0]辛烷-7-酮 | 63-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 中文名称: (1S,2R,3R,5S)-2,3,6-三羟基-4,8-二氧杂双环[3.3.0]辛烷-7-酮
• 英文名称: D-glucurono-6,3-lactone
• 英文别名: D-glucorono-γ-lactone；β-D-Glucofuranose-uronsaeure-δ-lacton；D-glucofuranurono-6,3-lactone；d-glucuronolactone；(2R,3R,3aR,6aR)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS: 63-29-6
• 化学式: C₆H₈O₆
• 分子量: 176.126
• InChiKey: OGLCQHRZUSEXNB-UAPNVWQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,5S)-2,3,6-三羟基-4,8-二氧杂双环[3.3.0]辛烷-7-酮 在 cation-exchange resin KU-2 、 氨 、 碳酸氢铵 作用下， 反应 16.33h， 生成 N-(β-D-glucuronopyranosyl)chloroacetamide
  参考文献：
  名称：

  Synthesis ofN-chioroacetyl-?-glycopyranosylamines, derivatives of monosaccharides and lactose

  摘要：

  N-Chloroacetyl-beta-glycosylamines were synthesized from various monosaccharides (hexoses, pentoses, deoxysugars, uronic acids, and sugar phosphates) and a disaccharide (lactose) by N-acylation of the corresponding beta-glycosylamines with chloroacetic anhydride in DMF. In some cases, treatment of monosaccharides with NH3 in the presence of (NH4)CO3 in MeOH or aqueous MeOH was more efficient than the methods previously described, as it gave beta-glycosylamines in higher yields.

  DOI：

  10.1007/bf01431821
• 作为产物：
  描述：

  (1S,2S)-安非他酮N-1’-脱氧-beta-D-葡萄糖醛酸 在 甲醇 作用下， 反应 0.08h， 以89%的产率得到(1S,2R,3R,5S)-2,3,6-三羟基-4,8-二氧杂双环[3.3.0]辛烷-7-酮
  参考文献：
  名称：

  非均相催化剂促进单糖的微波增强反应的当前观点

  摘要：

  据报道，与微波作为加热源协同作用，涉及非均相催化剂作为碳水化合物转化的促进剂。本文探讨了离子交换树脂，沸石，粘土和金属氧化物作为碳水化合物关键转化的便捷介体的应用。特别强调的是在无溶剂条件下使用（掺杂的）矿物载体作为清洁促进剂，并结合微波介电加热。

  DOI：

  10.1016/j.cattod.2011.01.001

文献信息

• A new method of acetonation with the zeolite HY as catalyst. Synthesis of O-Isopropylidene sugar derivatives
  作者：Amélia P. Rauter、Fernando Ramôa-Ribeiro、Ana C. Fernandes、JoséA. Figueiredo

  DOI：10.1016/0040-4020(95)00291-f

  日期：1995.6

  D-glucofuranurono-6,3-lactone, D-ribose and its methyl glycoside led to the formation of di-O- and/or mono-O-isopropylidene derivatives in yields from 37–75%. Reaction with D-galactose and L-arabinose afforded the synthesis of the corresponding furanose derivatives as major products, together with minor quantities of the thermodynamically more stable pyranose derivatives.

  事实证明，沸石HY是糖类丙酮化的合适催化剂。该方法由非常简单且经济的实验程序组成，其中催化剂可以回收并且可以再生。与D-半乳糖，L-阿拉伯糖，D-葡萄糖，D-木糖，L-山梨糖，D-葡萄糖呋喃呋喃诺-6,3-内酯，D-核糖及其甲基糖苷反应导致形成di- O-和/或单-O-异亚丙基衍生物的产率为37-75％。与D-半乳糖和L-阿拉伯糖的反应提供了相应的呋喃糖衍生物作为主要产物的合成，以及少量的热力学更稳定的吡喃糖衍生物。
• GLYCOSYLATED CHLORAMBUCIL ANALOGS AND USES THEREOF
  申请人：Thorson Jon S.

  公开号：US20120094946A1

  公开（公告）日：2012-04-19

  A library of glycosylated chlorambucil analogs which are useful as anti-tumor and/or anti-metastatic agents is disclosed. The glycosylated chlorambucil analogs have the general formula wherein represents a reducing sugar moiety.

  揭示了一种作为抗肿瘤和/或抗转移药物有用的葡萄糖基氯氨丁醇类似物的图书馆。这些葡萄糖基氯氨丁醇类似物具有一般公式，其中表示还原糖基团。
• Anionic furanose derivatives, methods of making and using the same
  申请人：Gordon; Paul

  公开号：US05358936A1

  公开（公告）日：1994-10-25

  A glucofuranose derivative substituted at the 3,5,6- or 3,6-positions with a radical that provides an anionic charge at physiological pH values is disclosed, as are pharmaceutical compositions, and methods of making and using the same. The compounds are useful in treating inflammation, and particularly conditions that involve neutrophil influx; they are also useful in inhibiting gastric ulcer formation.

  本发明揭示了一种在3,5,6-或3,6-位置被取代的含有阴离子电荷的基团的葡糖呋喃糖衍生物，以及制备和使用这些药物组合物的方法。这些化合物在治疗炎症，特别是涉及中性粒细胞浸涌的情况方面非常有用；它们还可用于抑制胃溃疡形成。
• [EN] THE TUMOR-SELECTIVE ANTI-CANCER PRODRUG BQC-G<br/>[FR] PROMÉDICAMENT ANTICANCÉREUX BQC-G SÉLECTIF DES TUMEURS
  申请人：ACADEMIA SINICA

  公开号：WO2011066418A1

  公开（公告）日：2011-06-03

  The invention relates to the synthesis of a second-generation camptothecin glucuronide prodrug (BQC-G) of a potent anticancer camptothecin derivative 5,6- dihydro-4H-benzo[de]quinoline-camptothecin (BQC). BQC-G was over 4000 times more water soluble than BQC, displayed good stability in human plasma and was an excellent substrate for enzymatic hydrolysis by bacterial and human β-glucuronidases. BQC-G was about 30 times less toxic than BQC, but was as toxic as BQC after hydrolysis of the glucuronide moiety by β-glucuronidase. In the presence of human serum albumin, BQC-G displayed lower cytotoxicity (IC50 = 1080 nM) but could be activated by β-glucuronidase to display potent activity (IC50 = 13.3 nM).

  该发明涉及合成一种第二代紧张素抗癌剂紧张素衍生物5,6-二氢-4H-苯并[de]喹啉-紧张素（BQC）的葡萄糖醛酸酯前药（BQC-G）。BQC-G的水溶性比BQC高出4000倍以上，在人类血浆中表现出良好的稳定性，并且是细菌和人类β-葡萄糖醛酸酶的优良底物。BQC-G的毒性比BQC低约30倍，但在β-葡萄糖醛酸酶水解葡萄糖醛酸基团后，其毒性与BQC相当。在人血清白蛋白存在的情况下，BQC-G表现出较低的细胞毒性（IC50 = 1080 nM），但可以被β-葡萄糖醛酸酶激活以显示出强效活性（IC50 = 13.3 nM）。
• METHODS TO QUENCH LIGHT FROM OPTICAL REACTIONS
  申请人：Daily William

  公开号：US20080248511A1

  公开（公告）日：2008-10-09

  The present invention relates to single and dual reporter luminescence assays utilizing reagents to quench an optical, e.g., an enzyme-mediated luminescence, reaction. In one embodiment of the invention, a reagent is added to an assay which selectively quenches a first enzyme-mediated luminescence reaction without affecting a subsequent distinct enzyme-mediated luminescent reaction(s). An assay kit containing one or more selective quench reagents, and compositions comprising the quench reagent(s), are also provided.

  本发明涉及使用试剂熄灭光学反应（例如酶介导的发光反应）的单一和双重报告发光测定法。在本发明的一个实施例中，向测定中添加试剂，该试剂有选择地熄灭第一种酶介导的发光反应，而不影响随后的不同酶介导的发光反应。还提供了包含一种或多种选择性熄灭试剂的测定试剂盒，以及包含熄灭试剂的组合物。