α-glucosyl chloride | 112531-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-glucosyl chloride
• 英文别名: alpha-d-Glucopyranosyl chloride；(2R,3R,4S,5S,6R)-2-chloro-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 112531-52-9
• 化学式: C₆H₁₁ClO₅
• 分子量: 198.603
• InChiKey: JPYHXSWNADKGBI-DVKNGEFBSA-N

物化性质

• 沸点：
  417.2±45.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 α-glucosyl chloride 以 丙酮 为溶剂， 反应 18.0h， 生成 甲基 Β-D-吡喃葡萄糖苷 、 alpha-甲基葡萄糖甙
  参考文献：
  名称：

  Protecting-group-free O-glysosidation using p-toluenesulfonohydrazide and glycosyl chloride donors

  摘要：

  A range of N '-glycosylsulfonohydrazides (GSHs) display good reactivity but poor stereoselectivity in protecting- group-free O-glycosidations when a moderate excess of the model acceptor n-decanol is employed. This stable, readily-accessed class of donor may be more tractable for the glycosylation of non-volatile acceptors than Fischer's glycosidation conditions. It is possible to generate unprotected glycosyl chlorides from GSHs in situ. In an effort to find conditions to improve glycosidation stereoselectivity, methanolysis of unprotected glucosyl chloride under halide-ion exchange conditions was examined. Relative to its tetra-O-benzyl analogue, this donor displays moderate, inverted stereoselectivity and a significantly faster reaction rate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.019
• 作为产物：
  描述：

  D-葡萄糖 在 N-溴代丁二酰亚胺(NBS) 、 四丁基氯化铵 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 生成 α-glucosyl chloride
  参考文献：
  名称：

  Protecting-group-free O-glysosidation using p-toluenesulfonohydrazide and glycosyl chloride donors

  摘要：

  A range of N '-glycosylsulfonohydrazides (GSHs) display good reactivity but poor stereoselectivity in protecting- group-free O-glycosidations when a moderate excess of the model acceptor n-decanol is employed. This stable, readily-accessed class of donor may be more tractable for the glycosylation of non-volatile acceptors than Fischer's glycosidation conditions. It is possible to generate unprotected glycosyl chlorides from GSHs in situ. In an effort to find conditions to improve glycosidation stereoselectivity, methanolysis of unprotected glucosyl chloride under halide-ion exchange conditions was examined. Relative to its tetra-O-benzyl analogue, this donor displays moderate, inverted stereoselectivity and a significantly faster reaction rate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.019

文献信息

• 1(Beta-D-Glycopyranosyl)-3-Substituted Nitrogenous Heterocyclic Compound, Medicinal Composition Containing the Same, and Medicinal Use Thereof
  申请人：Teranishi Hirotaka

  公开号：US20080139484A1

  公开（公告）日：2008-06-12

  A compound having SGLT1 and/or SGLT2 inhibitory activity which is usable as an agent for the prevention or treatment of diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications, obesity, etc. It is a 1-(β-D-glycopyranosyl)-3-substituted nitrogen-containing heterocyclic compound represented by the general formula (I), a prodrug, or a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof; an SGLT inhibitor containing the same; a pharmaceutical composition containing the same and a medicinal use thereof. In the formula, ring A represents optionally substituted aryl or heteroaryl; Q 1 to Q 5 independently represent a carbon atom having a hydrogen atom or substituent bonded thereto or a nitrogen atom; E represents a single bond, alkylene, —O—, —S— or —NH—; and R represents methyl, ethyl, fluoromethyl or hydroxymethyl.

  具有SGLT1和/或SGLT2抑制活性的化合物，可用作预防或治疗糖尿病、餐后高血糖、糖耐量受损、糖尿病并发症、肥胖等的药物。该化合物是一种1-(β-D-葡萄糖苷基)-3-取代的含氮杂环化合物，由通式(I)表示，是一种前药、药学上可接受的盐或其水合物或溶剂化物；还包括含有该化合物的SGLT抑制剂、含有该化合物的药物组合物和药用。在式中，环A代表可选取代的芳基或杂环基；Q1至Q5独立地表示具有氢原子或配基键合的碳原子或氮原子；E代表单键，烷基，-O-，-S-或-NH-；R代表甲基，乙基，氟甲基或羟甲基。
• NOVEL ANTI-INFLAMMATORY PRO-DRUGS
  申请人：Aerts Johannes Maria Franciscus Gerardus

  公开号：US20100323976A1

  公开（公告）日：2010-12-23

  The present invention relates to compounds according to formula (I): wherein R 2 is absent or a linking moiety and R 3 is selected from the group consisting of anti- inflammatory agents and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising compounds of formula (I) and the use of these pharmaceutical compositions for the treatment or prophylaxis of chronic inflammatory diseases, in particular those that are caused by chronically activated macrophages. The chronic inflammatory disease is in particular atherosclerosis, (rheumatoid) arthritis, an (auto) immune disease or sarcoidosis.

  本发明涉及式(I)的化合物，其中R2不存在或为连接基，R3选自抗炎剂及其药学上可接受的盐，包括式(I)的化合物的药物组合物以及这些药物组合物用于治疗或预防慢性炎症性疾病，特别是那些由长期活化的巨噬细胞引起的疾病。慢性炎症性疾病特别是动脉粥样硬化、(类风湿)关节炎、(自身)免疫性疾病或结节病。
• 1-( -D-GLYCOPYRANOSYL)-3-SUBSTITUTED NITROGENOUS HETEROCYCLIC COMPOUND, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL USE THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1803729A1

  公开（公告）日：2007-07-04

  A compound having SGLT1 and/or SGLT2 inhibitory activity which is usable as an agent for the prevention or treatment of diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications, obesity, etc. It is a 1-(β-D-glycopyranosyl)-3-substituted nitrogen-containing heterocyclic compound represented by the general formula (I), a prodrug, or a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof; an SGLT inhibitor containing the same; a pharmaceutical composition containing the same and a medicinal use thereof. In the formula, ring A represents optionally substituted aryl or heteroaryl; Q1 to Q5 independently represent a carbon atom having a hydrogen atom or substituent bonded thereto or a nitrogen atom; E represents a single bond, alkylene, -O-, -S- or -NH-; and R.represents methyl, ethyl, fluoromethyl or hydroxymethyl.

  一种具有 SGLT1 和/或 SGLT2 抑制活性的化合物，可用作预防或治疗糖尿病、餐后高血糖症、糖耐量受损、糖尿病并发症、肥胖症等的药物。它是由通式（I）代表的1-（β-D-吡喃甘露糖基）-3-取代的含氮杂环化合物、其原药或药学上可接受的盐，或其水合物或溶液；含有相同物质的SGLT抑制剂；含有相同物质的药物组合物及其药用用途。式中，环A代表任选取代的芳基或杂芳基；Q1至Q5独立地代表具有氢原子或取代基键合的碳原子或氮原子；E代表单键、亚烷基、-O-、-S-或-NH-；R.代表甲基、乙基、氟甲基或羟甲基。
• Composition containing stable vitamin B6 derivative
  申请人：Daiichi Fine Chemical Co., Ltd.

  公开号：EP2311847A1

  公开（公告）日：2011-04-20

  A compound represented by the following general formula (I) or a salt thereof: wherein R1 represents a glycosyl group, a phosphate group, or a phosphate group bound to R2; R2 represents -CH2OH, -CHO, -CH2NH2, CH2-amino acid residue, or -CH2-OPO2H; and R3 represents hydrogen atom, or -PO3H2, and a composition for cosmetics, medicaments, foodstuffs, and/or feeds containing the aforementioned compound or a salt thereof.

  由以下通式 (I) 代表的化合物或其盐： 其中R1代表糖基、磷酸基或与R2结合的磷酸基；R2代表-CH2OH、-CHO、-CH2NH2、CH2-氨基酸残基或-CH2-OPO2H；R3代表氢原子或-PO3H2，以及含有上述化合物或其盐的用于化妆品、药物、食品和/或饲料的组合物。
• Glycorandomization and production of novel vancomycin analogs
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20040259228A1

  公开（公告）日：2004-12-23

  The present invention provides combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.

  本发明提供了快速生成多种糖随机化结构库的组合方法，包括在糖基转移酶存在下培养一种或多种琼脂糖和NDP-糖池。糖基转移酶可以是与天然次生代谢物的生产有关或参与生产的糖基转移酶，也可以是推测与天然次生代谢物的生产有关或参与生产的糖基转移酶。糖基转移酶在其 NDP-糖供体和/或其糖醛酸方面可以表现出很大的灵活性。NDP 糖供体可以从市场上买到，也可以通过利用突变型或野生型核苷酸转移酶对底物的极大灵活性来生产。