ethyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside | 172146-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside
• 英文别名: ethyl 6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside；[(3aS,4R,6S,7R,7aS)-6-ethylsulfanyl-7-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 172146-97-3
• 化学式: C₂₅H₄₂O₆SSi
• 分子量: 498.756
• InChiKey: JWLGZYMZBVKUFX-YSFPZDHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-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 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 1.5h， 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 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 ethyl 6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-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

• Sulfated .alpha.-glycolipid derivatives as cell adhesion inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US05663151A1

  公开（公告）日：1997-09-02

  There is provided novel sulfated .alpha.-glycolipid compounds of the formula ##STR1## wherein R is an acyl residue of a fatty acid; R.sup.1 is --(CH.dbd.CH).sub.m --(CH.sub.2).sub.n --CH.sub.3 ; R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are independently at least two --SO.sub.3 H; R.sup.2, R.sup.3, R.sup.4 R.sup.5 and R.sup.6 each are independently hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from halogen, C.sub.1-4 alkyl, trifluoromethyl, hydroxy and C.sub.1-4 alkoxy; m is an integer of 0 or 1; n is 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.

  提供了一种新型的磺酸化α-糖脂化合物，其化学式为##STR1##其中R是脂肪酸的酰基残基；R.sup.1是--(CH.dbd.CH).sub.m--(CH.sub.2).sub.n--CH.sub.3；R.sup.2、R.sup.3、R.sup.4和R.sup.6独立地至少有两个--SO.sub.3 H；R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6各自独立地是氢、未取代或取代的烷酰基、芳基烷基或芳基羰基，其中所述取代基选自卤素、C.sub.1-4烷基、三氟甲基、羟基和C.sub.1-4烷氧基；m是0或1的整数；n是从5到14的整数，包括在内；或其非毒性药学上可接受的盐、溶剂化合物或水合物，它们是选择素介导的细胞粘附的抑制剂，并且在哺乳动物的炎症性疾病和其他病理条件的治疗或预防中是有用的。
• 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.