2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl trichloroacetimidate | 670249-42-0

• 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-galactopyranosyl trichloroacetimidate
• 英文别名: O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)trichloroacetimidate；pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)][pivaloyl(-6)]Gal(b)-O-C(NH)CCl3；[(2R,3S,4S,5R,6S)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 670249-42-0
• 化学式: C₂₈H₄₄Cl₃NO₁₀
• 分子量: 661.017
• InChiKey: WOSWCYLUSZNKFK-ICUGJSFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 、 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(2S,3R,4E)-2-azido-3-benzoyloxy-1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyloxy)octadec-4-ene
  参考文献：
  名称：

  CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety

  摘要：

  Native sulfatide (a mixture of 3-sulfated beta-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture and bear palmitic, stearic, behenic or nervonic fatty acid chains, is described. Azidosphingosine was stereoselectively synthesized through a CuCN-catalyzed allylic alkylation of a hexenitol dimesylate derived from D-xylose; beta-glycosylation of azidosphingosine, with a suitable D-galactosyl trichloroacetimidate led, after reduction of the azido, group, to the galactosylsphingosine skeleton, which was derivatized with the different fatty acids. Final regioselective 3-sulfation gave the desired sulfatides, which were tested for activation of sulfatide-specific and CD1a-restricted T-cell clones. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01092-x
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose 在 potassium carbonate 、 肼 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Regioselective Glycosylation of Glucosamine and Galactosamine Derivates Using O-Pivaloyl Galactosyl Donors

  摘要：

  Penta-O-pivaloyl-galactopyranose和tetra-O-pivaloyl-galactopyranosyl溴在亲电活化后与6-O-保护的2-azido-galactosides反应，高选择性地形成Thomsen-Friedenreich抗原二糖的前体结构，但产率较低。使用4,6-Obenzylidene保护的2-azidogalactosides和2-O-pivaloyl苯硫基半乳苷，可以得到这种类型的T-抗原二糖，产率较高。4,6-O-benzylidene保护的葡萄糖氨基衍生物与O-pivaloyl保护的半乳苷溴的糖基化反应有效地产生了乳糖氨二糖。甚至通过这种方法，一种硫代糖苷也可以有效地被半乳苷化，形成一种作为潜在糖基供体的二糖硫代糖苷。

  DOI：

  10.1515/znb-2003-0808

文献信息

• Fused heterocyclic derivative, medicinal composition containing the same, and medicinal use thereof
  申请人：Fushimi Nobuhiko

  公开号：US20060247179A1

  公开（公告）日：2006-11-02

  The present invention provides fused heterocyclic derivatives represented by the general formula: wherein R 1 represents H, halogen, OH, etc.; R 2 represents H, halogen or an alkyl group; R 3 and R 4 represent H, OH, halogen, etc.; Q represents alkylene, etc.; ring A represents aryl or heteroaryl; and G represents , or pharmaceutically acceptable salts thereof, or prodrugs thereof, which exhibit an excellent inhibitory activity in human SGLT and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications or obesity, pharmaceutical compositions comprising the same, and pharmaceutical uses thereof.

  本发明提供了由通式表示的融合杂环衍生物：其中R1代表H、卤素、OH等；R2代表H、卤素或烷基；R3和R4代表H、OH、卤素等；Q代表烷基等；环A代表芳基或杂芳基；G代表，或其药学上可接受的盐，或其前药，它们在人类SGLT中表现出优异的抑制活性，并且可用作预防或治疗与高血糖有关的疾病，如糖尿病、餐后高血糖、糖耐量受损、糖尿病并发症或肥胖症的药剂，以及它们的药用组合物和药用用途。
• FUSED HETEROCYCLIC DERIVATIVE, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL USE THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1609798B1

  公开（公告）日：2012-05-09
• US7566699B2
  申请人：——

  公开号：US7566699B2

  公开（公告）日：2009-07-28
• CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety
  作者：Federica Compostella、Laura Franchini、Gennaro De Libero、Giovanni Palmisano、Fiamma Ronchetti、Luigi Panza

  DOI：10.1016/s0040-4020(02)01092-x

  日期：2002.10

  Native sulfatide (a mixture of 3-sulfated beta-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture and bear palmitic, stearic, behenic or nervonic fatty acid chains, is described. Azidosphingosine was stereoselectively synthesized through a CuCN-catalyzed allylic alkylation of a hexenitol dimesylate derived from D-xylose; beta-glycosylation of azidosphingosine, with a suitable D-galactosyl trichloroacetimidate led, after reduction of the azido, group, to the galactosylsphingosine skeleton, which was derivatized with the different fatty acids. Final regioselective 3-sulfation gave the desired sulfatides, which were tested for activation of sulfatide-specific and CD1a-restricted T-cell clones. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Regioselective Glycosylation of Glucosamine and Galactosamine Derivates Using O-Pivaloyl Galactosyl Donors
  作者：Mathia Oßwald、Uwe Lang、Siglinde Friedrich-Bochnitschek、Waldemar Pfrengle、Horst Kunz

  DOI：10.1515/znb-2003-0808

  日期：2003.8.1

  Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield.With 4,6-Obenzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.

  Penta-O-pivaloyl-galactopyranose和tetra-O-pivaloyl-galactopyranosyl溴在亲电活化后与6-O-保护的2-azido-galactosides反应，高选择性地形成Thomsen-Friedenreich抗原二糖的前体结构，但产率较低。使用4,6-Obenzylidene保护的2-azidogalactosides和2-O-pivaloyl苯硫基半乳苷，可以得到这种类型的T-抗原二糖，产率较高。4,6-O-benzylidene保护的葡萄糖氨基衍生物与O-pivaloyl保护的半乳苷溴的糖基化反应有效地产生了乳糖氨二糖。甚至通过这种方法，一种硫代糖苷也可以有效地被半乳苷化，形成一种作为潜在糖基供体的二糖硫代糖苷。