ethyl 2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside | 172146-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside
• 英文别名: ethyl 2-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside；(2R,3R,4S,5R,6S)-6-ethylsulfanyl-2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]oxane-3,4-diol
• CAS: 172146-98-4
• 化学式: C₁₆H₂₄O₆S
• 分子量: 344.429
• InChiKey: HVEGKKMZBHBESF-CWVYHPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 potassium tert-butylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 生成 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-p-methoxybenzyl-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene
  参考文献：
  名称：

  Novel mimics of sialyl Lewis X

  摘要：

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00015-3
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 ethyl 2-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Novel mimics of sialyl Lewis X

  摘要：

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00015-3

文献信息

• Synthesis of three tethered trisaccharides to probe entropy contributions in carbohydrate—protein interactions
  作者：Ping Zhang、David R. Bundle

  DOI：10.1560/yxqt-2jju-ylaa-l04q

  日期：2000.12

  trisaccharides are biologically inactive due to distorted conformations that cannot be accommodated in the antibody binding site. Trisaccharide 4 is active since both hydroxymethyl groups of galactose and mannose are solvent exposed in the bound state and the constrained conformation of 4 is virtually superimposable on the bound conformation of 1. Despite the retained complimentary and significant reduction

  晶体结构数据表明，支链三糖1构成了沙门氏菌血清群B抗原的完全抗原决定簇，该抗原决定簇被单克隆抗体SE155.4识别。为了表征与在结合状态下固定糖苷扭转角相关的熵成本，已经合成了该三糖2-4的三种不同的分子内束缚类似物。两个三糖通过3,6-二脱氧己糖的O-2位置通过亚甲基乙缩醛进行束缚，后者与半乳糖（2）的O- 2或甘露糖（3）的O-4相当。第三根系绳，α，α′-二硫代-p-二甲苯，跨越甘露糖和半乳糖残基的C-6原子，以创建三糖4。2和3的缩醛系链跨越了羟基中心，已知与分子内糖-糖氢键有关，但是由于不能容纳在抗体结合位点的扭曲构象，这两种三糖都没有生物学活性。三糖4是有活性的，因为半乳糖和甘露糖的羟甲基都在结合状态下暴露于溶剂，并且4的约束构象实际上与1的结合构象重叠。尽管保留了互补性并显着降低了扭转柔韧性，但三糖4个表现出Δ ģ °= -7.6千卡摩尔-1相比Δ ģ °= -7.1千卡摩尔
• Sulfated alpha-glycolipid derivatives as cell adhesion inhibitors
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0671407A2

  公开（公告）日：1995-09-13

  There is provided novel sulfated α-glycolipid compounds of the formula wherein Ris an acyl residue of a fatty acid; R¹is -(CH=CH)m-(CH₂)n-CH₃; R², R³, R⁴ and R⁶are independently at least two -SO₃H; R², R³, R⁴ R⁵ and R⁶each are independently hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from halogen, C₁₋₄ alkyl, trifluoromethyl, hydroxy and C₁₋₄ alkoxy; mis an integer of 0 or 1; nis an integer of from 5 to 14, inclusive; or a non-toxic pharmaceutically acceptable salt, solvate or hydrate thereof which are inhibitors of selectin-mediated cellular adhesion and are useful in the treatment or prevention of inflammatory diseases and other pathological conditions in mammals.

  本发明提供了新型硫酸化 α-糖脂化合物，其式为 式中 是脂肪酸的酰基残基； R¹为-(CH=CH)m-(CH₂)n-CH₃； R²、R³、R⁴ 和 R⁶ 独立地为至少两个-SO₃H； R²、R³、R⁴、R⁵ 和 R⁶ 各自独立地为氢、未取代或取代的烷酰基、芳烷基或芳羰基，其中所述取代基选自卤素、C₁₋₄ 烷基、三氟甲基、羟基和 C₁₋₄ 烷氧基； mis 是 0 或 1 的整数； n 是 5 至 14（包括 14）的整数； 或其无毒的药学上可接受的盐、溶液或水合物，它们是选择素介导的细胞粘附的抑制剂，可用于治疗或预防哺乳动物的炎症性疾病和其它病理状况。
• US5663151A
  申请人：——

  公开号：US5663151A

  公开（公告）日：1997-09-02
• US5747463A
  申请人：——

  公开号：US5747463A

  公开（公告）日：1998-05-05
• Novel mimics of sialyl Lewis X
  作者：Anne Marinier、Alain Martel、Carol Bachand、Serge Plamondon、Brigitte Turmel、Jean-Paul Daris、Jacques Banville、Philippe Lapointe、Carl Ouellet、Pierre Dextraze、Marcel Menard、John J.K Wright、Julie Alford、Debbie Lee、Paul Stanley、Xina Nair、Gordon Todderud、Kenneth M Tramposch

  DOI：10.1016/s0968-0896(01)00015-3

  日期：2001.6

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.