2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosylbromide | 958300-05-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosylbromide
• 英文别名: (2R,3R,4S,5R,6R)-2-bromo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyltris(2,2-dimethylpropanoate)；(2S,3R,4S,5R,6R)-2-Bromo-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)；[(2R,3R,4S,5R,6S)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 958300-05-5
• 化学式: C₂₆H₄₃BrO₉
• 分子量: 579.526
• InChiKey: BSDBCYHGMPHOAL-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosylbromide 在 哌啶 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.25h， 生成 (Z)-1-phenyl-3-[4-oxo-2-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosylsulfanyl)-4,5-dihydro-thiazol-5-ylidene]indolin-2-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of (Z)-1-glycosyl-3-(5-oxo-2-thioxoimidazolidin-4-ylidene)indolin-2-ones and (Z)-3-(2-glycosylsulfanyl-4-oxo-4,5-dihydro-thiazol-5-ylidene)indolin-2-ones

  摘要：

  N-糖苷化的异靛蓝与咪唑酮和噻唑酮的反应生成N-糖苷化的(Z)-1-糖苷-3-(5-氧-2-硫喹唑啉-4-亚基)吲哚-2-酮。S-糖苷化的噻唑酮与异靛蓝反应生成S-糖苷化的(Z)-3-(2-糖苷硫酰基-4-氧-4,5-二氢噻唑-5-亚基)吲哚-2-酮。这些分子代表了药理学上重要的混合结构，包括碳水化合物、异靛蓝、2-硫脲、伪硫脲和罗丹宁。产品对肺癌细胞系H157表现出良好且选择性的活性。含有葡萄糖基团的3-(5-氧-2-硫喹唑啉-4-亚基)吲哚-2-酮具有最佳活性。

  DOI：

  10.1039/c3ra44362k

文献信息

• PROCESS FOR THE PREPARATION OF COMPOUNDS USEFUL AS INHIBITORS OF SGLT2
  申请人：FARINA Vittorio

  公开号：US20110087017A1

  公开（公告）日：2011-04-14

  The present invention is directed to a novel process for the preparation of compounds having inhibitory activity against sodium-dependent glucose transporter (SGLT) being present in the intestine or kidney.

  本发明涉及一种新型制备具有抑制钠依赖型葡萄糖转运蛋白（SGLT）活性的化合物的方法，该蛋白存在于肠道或肾脏中。
• PROCESS FOR PRODUCTION OF GLUCOPYRANOSYLOXYPYRAZOLE DERIVATIVE
  申请人：Kasai Kiyoshi

  公开号：US20090062518A1

  公开（公告）日：2009-03-05

  The present invention relates to a method for preparing the glucopyranosyloxypyrazole derivatives which are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications, obesity or the like. A glucopyranosyloxypyrazole derivative can be easily and efficiently prepared by allowing a benzylpyrazole derivative represented by the general formula: wherein R 1 , R 2 , R 3 , R 4 and R 5 may be the same or different, for example each of them is a hydrogen atom, a halogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, R 6 is an alkyl group, for example R 7 is a hydrogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, to react with a compound represented by the general formula: wherein as an example, PG 1 is a pivaloyl group or the like, as an example, X 1 is a bromine atom or the like, therefore the present invention is extremely useful as a method for preparing pharmaceutical compounds.

  本发明涉及一种制备葡萄糖吡唑氧基吡唑衍生物的方法，该衍生物可用作预防或治疗与高血糖相关的疾病，如糖尿病、糖尿病并发症、肥胖症等的药物。通过让一个苄基吡唑衍生物与一个化合物反应，可以轻松高效地制备葡萄糖吡唑氧基吡唑衍生物。其中，该苄基吡唑衍生物由下列通式表示：其中R1、R2、R3、R4和R5可以相同也可以不同，例如每个都是氢原子、卤素原子或烷基、烷氧基、芳基甲氧基等，R6是烷基，例如R7是氢原子或烷基、烷氧基、芳基甲氧基等。化合物由下列通式表示：其中，PG1是一个Pivaloyl基团或类似物，例如，X1是溴原子或类似物。因此，本发明作为一种制备药物化合物的方法非常有用。
• Process for production of glucopyranosyloxypyrazole derivative
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：US08022192B2

  公开（公告）日：2011-09-20

  The present invention relates to a method for preparing the glucopyranosyloxypyrazole derivatives which are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications, obesity or the like. A glucopyranosyloxypyrazole derivative can be easily and efficiently prepared by allowing a benzylpyrazole derivative represented by the general formula: wherein R1, R2, R3, R4 and R5 may be the same or different, for example each of them is a hydrogen atom, a halogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, R6 is an alkyl group, for example R7 is a hydrogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, to react with a compound represented by the general formula: wherein as an example, PG1 is a pivaloyl group or the like, as an example, X1 is a bromine atom or the like, therefore the present invention is extremely useful as a method for preparing pharmaceutical compounds.

  本发明涉及一种制备葡萄糖吡唑基氧代吡唑衍生物的方法，该衍生物可用作预防或治疗与高血糖相关的疾病，如糖尿病、糖尿病并发症、肥胖症等的药物。通过让一种由下式表示的苄基吡唑衍生物与下式表示的化合物反应，可以轻松高效地制备葡萄糖吡唑基氧代吡唑衍生物：其中R1、R2、R3、R4和R5可能相同或不同，例如它们中的每一个是氢原子、卤素原子或烷基、烷氧基、芳基甲氧基基团等，R6是烷基，例如R7是氢原子或烷基、烷氧基、芳基甲氧基基团等。例如，PG1是肉桂酰基等，X1是溴原子等。因此，本发明作为一种制备药物化合物的方法极为有用。
• Synthesis of menarandroside A from dehydroepiandrosterone
  作者：Samuel D. Offei、Hadi D. Arman、Francis K. Yoshimoto

  DOI：10.1039/d3ob00054k

  日期：——

  the synthesis of menarandroside A from dehydroepiandrosterone (DHEA). Key features of this synthesis include: (i) Wittig reaction of the C17-ketone of a 12-oxygenated DHEA derivative to introduce the C17-acetyl moiety, and (ii) the stereoselective reduction of a C12-keto intermediate bearing an sp2-center at C17 to yield the C12α-hydroxy group. In addition, an oxidation of a methyl enol ether derivative

  Menarandroside A 带有 12α-羟基孕烯醇酮类固醇骨架，是从植物Cynanchum menarandrense中分离出来的。用这种含有美那糖苷 A 的植物提取物对分泌素肿瘤细胞系 (STC-1) 肠细胞进行处理，导致胰高血糖素样肽 1 (GLP-1) 的分泌增加，这种肽在血液调节中发挥作用糖水平。GLP-1的升高有利于2型糖尿病的治疗。我们公开了从脱氢表雄酮 (DHEA) 合成 menarandroside A。该合成的主要特征包括：(i) 12-氧化 DHEA 衍生物的 C17-酮的 Wittig 反应引入 C17-乙酰基部分，以及 (ii) 带有 sp 2的 C12-酮中间体的立体选择性还原-中心位于 C17 以产生 C12α-羟基。此外，还发现了使用四丙基过钌酸铵 (TPAP) 和N-甲基-吗啉-N-氧化物 (NMO) 将甲基烯醇醚衍生物氧化为 α-羟基甲酯。
• Synthesis of Unsymmetrical Trisulfides from S‐Substituted Sulphenylthiosulphates
  作者：Shuaishuai Liang、Liye Ma、Zihao Guo、Fanmin Liu、Zijian Lin、Wenbin Yi

  DOI：10.1002/anie.202404139

  日期：2024.7.8

  efficient approach for accessing unsymmetrical trisulfides through an I2-catalyzed three-component coupling of S-substituted sulphenylthiosulphates (RSSSO3Na), alkyl electrophiles and thiourea. This is the first report on utilizing RSSSO3Na as disulfurating reagent and provides a convenient method for converting bromides, chlorides, iodides and tosylates into trisulfides.

  我们开发了一种通用且有效的方法，通过 I 2催化的S取代的磺基硫代硫酸盐 (RSSSO 3 Na)、烷基亲电子试剂和硫脲的三组分偶联来获取不对称三硫化物。这是第一篇利用RSSSO 3 Na作为二硫化试剂的报道，并提供了一种将溴化物、氯化物、碘化物和甲苯磺酸盐转化为三硫化物的便捷方法。