ethyl 2-O-benzoyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside | 161765-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-benzoyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxy-2-ethoxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 161765-91-9
• 化学式: C₃₅H₃₉NO₁₆
• 分子量: 729.692
• InChiKey: MHIOYQPIHXWPGV-BODBPOCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  220
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 、 ethyl 2-O-benzoyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside 在 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 生成 ethyl 3,6-bis-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs

  摘要：

  Several sialyl Lewis x dimers anchored onto a galactose template or attached to 1,4-butanediol or 1,5-pentanediol have been prepared chemoenzymatically and evaluated as inhibitors of E-selectin-mediated cell adhesion. Two monosaccharide units were simultaneously incorporated (i.e., Gal, NeuAc, Fuc) by a glycosyltransferase into a chemically synthesized core structure containing GlcNAc and Gal. Each of the galactose-anchored dimers had higher activity than the sialyl Lewis x pentasaccharide la, with the general trend being 3,6-linked > 2,3 greater than or equal to 4,6 greater than or equal to 2,6 monomer. The dimers linked to butanediol or pentanediol showed the same level of activity as the pentasaccharide monomer. Conformational analysis of these dimers with NMR indicated that each sialyl Lewis x domain of the dimers retains the same conformation as the monomer. The differences in activity of the dimers most likely derive from differences in the relative orientation and distance between the monomer domains, suggesting the importance of the linker used in the preparation of dimers.

  DOI：

  10.1021/ja00106a008
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside 在 溶剂黄146 作用下， 反应 0.5h， 以80%的产率得到ethyl 2-O-benzoyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs

  摘要：

  Several sialyl Lewis x dimers anchored onto a galactose template or attached to 1,4-butanediol or 1,5-pentanediol have been prepared chemoenzymatically and evaluated as inhibitors of E-selectin-mediated cell adhesion. Two monosaccharide units were simultaneously incorporated (i.e., Gal, NeuAc, Fuc) by a glycosyltransferase into a chemically synthesized core structure containing GlcNAc and Gal. Each of the galactose-anchored dimers had higher activity than the sialyl Lewis x pentasaccharide la, with the general trend being 3,6-linked > 2,3 greater than or equal to 4,6 greater than or equal to 2,6 monomer. The dimers linked to butanediol or pentanediol showed the same level of activity as the pentasaccharide monomer. Conformational analysis of these dimers with NMR indicated that each sialyl Lewis x domain of the dimers retains the same conformation as the monomer. The differences in activity of the dimers most likely derive from differences in the relative orientation and distance between the monomer domains, suggesting the importance of the linker used in the preparation of dimers.

  DOI：

  10.1021/ja00106a008

文献信息

• Bivalent sialyl X saccharides
  申请人：Cytel Corporation

  公开号：US05559103A1

  公开（公告）日：1996-09-24

  The present invention relates to bivalent sialyl Lewis X saccharide compounds that inhibit cellular binding to a selectin receptor. Pharmaceutical compositions containing a compound of Formula I, and processes for making and using the same are disclosed. A contemplated bivalent sialyl Lewis X saccharide compound has a structure that corresponds to Formula I, below, ##STR1## wherein R is a directly linked divalent monosaccharide unit; Y is selected from the group consisting of C(O), SO.sub.2, HNC(O), OC(O) and SC(O); R.sup.2 is selected from the group consisting of a C.sub.1 -C.sub.6 hydrocarbyl, an aryl, a substituted aryl and a phenyl C.sub.1 -C.sub.3 alkylene group, wherein an aryl group has one six-membered aromatic ring or two fused six-membered aromatic rings, which ring or rings are hydrocarbyl, monoazahydrocarbyl, or diazahydrocarbyl rings, and a substituted aryl group is a before-mentioned aryl group having a substituent selected from the group consisting of halo, trifluoromethyl, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, amino, mono-C.sub.1 -C.sub.6 alkylamino, di-C.sub.1 -C.sub.6 alkylamino, benzylamino and C.sub.1 -C.sub.6 alkylbenzylamino; R.sup.3 is methyl or hydroxymethyl; X is selected from the group consisting of hydroxyl, C.sub.1 -C.sub.6 acyloxy, C.sub.2 -C.sub.6 hydroxylacyloxy, halo and azido; Z.sup.1 and Z.sup.2 are .alpha.-L-fucosyl or hydrogen (H), but at least one of Z.sup.1 and Z.sup.2 is .alpha.-L-fucosyl; and M is a proton (H.sup.+) or a pharmaceutically acceptable cation.

  本发明涉及双价唾液酸-Lewis X糖类化合物，其抑制细胞与选择素受体的结合。本发明揭示了含有式I化合物的制药组合物以及制备和使用该化合物的过程。所考虑的双价唾液酸-Lewis X糖类化合物具有如下的结构式I，其中R是直接连接的双价单糖单元；Y选自C（O），SO.sub.2，HNC（O），OC（O）和SC（O）组成的群；R.sup.2选自C.sub.1-C.sub.6烃基，芳基，取代芳基和苯基C.sub.1-C.sub.3烷基，其中芳基基团具有一个六元环芳香环或两个融合的六元环芳香环，该环或环是烃基，单氮杂烃基或双氮杂烃基环，取代芳基基团是前述芳基基团，其取代基选自卤素，三氟甲基，硝基，C.sub.1-C.sub.6烷基，C.sub.1-C.sub.6烷氧基，氨基，单C.sub.1-C.sub.6烷基氨基，双C.sub.1-C.sub.6烷基氨基，苄基氨基和C.sub.1-C.sub.6烷基苄基氨基；R.sup.3是甲基或羟甲基；X选自羟基，C.sub.1-C.sub.6酰氧基，C.sub.2-C.sub.6羟基酰氧基，卤素和偶氮基；Z.sup.1和Z.sup.2是α-L-岩藻糖基或氢（H），但至少一个Z.sup.1和Z.sup.2是α-L-岩藻糖基；M是质子（H.sup.+）或药学上可接受的阳离子。
• ENZYMATIC SYNTHESIS OF GLYCOSIDIC LINKAGES
  申请人：Neose Technologies, Inc.

  公开号：EP0820519B1

  公开（公告）日：2001-01-03
• US5559103A
  申请人：——

  公开号：US5559103A

  公开（公告）日：1996-09-24
• US5576305A
  申请人：——

  公开号：US5576305A

  公开（公告）日：1996-11-19
• US5728554A
  申请人：——

  公开号：US5728554A

  公开（公告）日：1998-03-17