2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose | 144102-44-3

• 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-glucopyranose
• 英文别名: pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)][pivaloyl(-6)]b-Glc；[(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-hydroxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 144102-44-3
• 化学式: C₂₆H₄₄O₁₀
• 分子量: 516.629
• InChiKey: JYGDPQMHICAXOT-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 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：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose 在 甲醇 、 sodium methylate 、 caesium carbonate 作用下， 生成 testosterone-β-D-glucopyranoside
  参考文献：
  名称：

  A novel synthesis of protected glucose intermediates.

  摘要：

  The 1,2,4,6-Tetra-O-pivaloyl-D-gluco-pyranose 3 and 1,2,3,6-Tetra-O-pivaloyl-D-glucopyranose 4 have been prepared in one step from anhydrous glucose and pivaloyl chloride. These new intermediates can be converted into the corresponding esters, or used in the synthesis of a disaccharide in good yield. Thus, 2,3,6-Tri-O-pivaloyl-gluco-pyranose 10 can be prepared from 4, and used for preparation of beta-gluco derivatives via the corresponding trichloroacetimidate 12.

  DOI：

  10.1016/s0040-4039(00)61283-2
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-6-((新戊酰氧基)甲基)四氢-2H-吡喃-2,3,4,5-四 在 乙酸肼 作用下， 生成 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose
  参考文献：
  名称：

  A novel synthesis of protected glucose intermediates.

  摘要：

  The 1,2,4,6-Tetra-O-pivaloyl-D-gluco-pyranose 3 and 1,2,3,6-Tetra-O-pivaloyl-D-glucopyranose 4 have been prepared in one step from anhydrous glucose and pivaloyl chloride. These new intermediates can be converted into the corresponding esters, or used in the synthesis of a disaccharide in good yield. Thus, 2,3,6-Tri-O-pivaloyl-gluco-pyranose 10 can be prepared from 4, and used for preparation of beta-gluco derivatives via the corresponding trichloroacetimidate 12.

  DOI：

  10.1016/s0040-4039(00)61283-2

文献信息

• Pivaloyl-protected glucosyl iodide as a glucosyl donor for the preparation of β-C-glucosides
  作者：Virginia V. Triantakonstanti、Alexandros Toskas、Nicolaos S. Iordanidis、Thanos Andreou、Theoharis V. Koftis、John K. Gallos

  DOI：10.1016/j.tetlet.2020.152173

  日期：2020.7

  A method for the selective synthesis of β-C-glucosides using α-D-tetra-O-pivaloylglucosyl iodide as a glucosyl donor is reported. Its diastereoselectivity differs from that of the respective acetyl-protected glucosyl bromide, as it reported in the literature under similar reaction conditions. The concentration of the catalyst, the solvent and the type of additive used are crucial factors that determine

  报道了一种使用α - D-四-O-新戊酰葡糖基碘化物作为葡糖基供体来选择性合成β - C-葡糖苷的方法。如文献中报道的，在相似的反应条件下，它的非对映选择性不同于相应的乙酰基保护的葡糖基溴。催化剂的浓度，溶剂和所用添加剂的类型是决定反应选择性的关键因素。该方法已用于dapagliflozin的短合成中。α - D-四-O-新戊酰葡萄糖基碘在CDCl 3中的稳定性还研究了回流下的THF。分离和表征了偶联和分解反应中的所有副产物，并提出了其形成的可能途径。
• NEUROTOXIC STEROL GLYCOSIDES
  申请人：Shaw Christopher Ariel

  公开号：US20110280805A1

  公开（公告）日：2011-11-17

  The invention relates to compositions for use in animal models of neurodegenerative disease and methods therefor. More particularly, the invention relates to the use of neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof, in animal models of neurodegenerative disease. Neurotoxicity-modulating chromenols can also be used in these animal models in combination with the neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof.

  这项发明涉及用于神经退行性疾病动物模型的组合物和方法。更具体地说，该发明涉及在神经退行性疾病动物模型中使用神经毒性甾醇糖苷或神经毒性糖脂，或二者的组合。神经毒性调节色酚也可以与神经毒性甾醇糖苷或神经毒性糖脂或二者的组合在这些动物模型中使用。
• A New Base-Labile Anchoring Group for Polymer-Supported Oligosaccharide Synthesis
  作者：Yali Wang、Hong Zhang、Wolfgang Voelter

  DOI：10.1246/cl.1995.273

  日期：1995.4

  A new base-labile 9-hydroxymethylfluorene-2-succinic acid-based anchoring group, coupled to amino-ethylated polyethylene glycol, opens a new approach for polymer-supported syntheses of oligosaccharides using phenyl 1-thioglycopyranoside sulfoxides as highly efficient glycosyl donors.

  一种新的基于碱不稳定的 9-羟甲基芴-2-琥珀酸锚定基团，与氨基乙基化聚乙二醇偶联，为使用苯基 1-硫代糖基吡喃亚砜作为高效糖基供体合成聚合物支持的寡糖开辟了新途径。
• Pyrazole derivatives, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof
  申请人：Fushimi Nobuhiko

  公开号：US20050272669A1

  公开（公告）日：2005-12-08

  The present invention provides pyrazole derivatives represented by the general formula: wherein R 1 represents H, an optionally substituted C 1-6 alkyl group etc.; one of Q and T represents a group represented by the general formula: or a group represented by the general formula: while the other represents an optionally substituted C 1-6 alkyl group etc.; R 2 represents H, a halogen atom, OH, an optionally substituted C 1-6 alkyl group etc.; X represents a single bond, O or S; Y represents an optionally substituted C 1-6 alkylene group etc.; Z represents —R B , —COR C etc. in which R B represents an optionally substituted C 1-6 alkyl group etc.; and R C represents an optionally substituted C 1-6 alkyl group etc.; R 4 represents H, an optionally substituted C 1-6 alkyl group etc.; and R 3 , R 5 and R 6 represent H, a halogen atom etc., pharmaceutically acceptable salts thereof or prodrugs thereof, which exhibit an excellent inhibitory activity in human SGLT1 and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, impaired glucose tolerance, impaired fasting glycemia, diabetic complications or obesity, and a disease associated with the increase of blood galactose level such as galactosemia, and pharmaceutical compositions comprising the same, pharmaceutical uses thereof, and intermediates for production thereof.

  本发明提供了由通式表示的吡唑衍生物：其中，R1代表H、可选取代的C1-6烷基等；Q和T中的一个代表由通式表示的基团：或由通式表示的基团：另一个代表可选取代的C1-6烷基等；R2代表H、卤素原子、OH、可选取代的C1-6烷基等；X代表单键、O或S；Y代表可选取代的C1-6亚烷基等；Z代表-RB、-CORC等，其中RB代表可选取代的C1-6烷基等；RC代表可选取代的C1-6烷基等；R4代表H、可选取代的C1-6烷基等；R3、R5和R6代表H、卤素原子等，其药学上可接受的盐或前药，具有在人类SGLT1中出色的抑制活性，可用作预防或治疗与高血糖相关的疾病，如糖尿病、糖耐量受损、空腹血糖受损、糖尿病并发症或肥胖症，以及与血中半乳糖水平增加相关的疾病，如半乳糖血症的治疗剂，以及包含它们的制药组合物、制药用途和制备它们的中间体。
• Stereoselective oxidative <i>O</i>-glycosylation of disarmed glycosyl iodides with alcohols using PIDA as the promoter
  作者：Maria A. Boulogeorgou、Alexandros Toskas、John K. Gallos、Christos I. Stathakis

  DOI：10.1039/d3ob00929g

  日期：——

  The direct and practical oxidative anomeric O-glycosylation of glycosyl iodides with an array of alcohols as glycosyl acceptors is presented. Using phenyliodine(III) diacetate (PIDA) as the promoter of the reaction, at ambient temperature, an enviromentally benign and operationally simple protocol has been developed providing access stereoselectively to 1,2-trans-O-glycosides.

  提出了用一系列醇作为糖基受体对糖基碘化物进行直接且实用的氧化异头O-糖基化。使用二乙酸苯碘( III ) (PIDA)作为反应促进剂，在环境温度下，开发了一种环境友好且操作简单的方案，提供立体选择性地获得1,2-反式-O-糖苷。