ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 71048-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: 8-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS: 71048-95-8
• 化学式: C₂₅H₃₇NO₈
• 分子量: 479.571
• InChiKey: MLVKBOGVBGQTML-SIEBBHQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -30.0~-10.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 8-methoxycarbonyloctyl 4-deoxy-β-D-xylo-hexopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Recognition of β-d-Gal p-(1 → 3)-β-d-Glc pNAc-OR acceptor analogues by the Lewis α-(1 → 34)-fucosyltransferase from human milk

  摘要：

  The Lewis alpha-(1 --> 3/4)-frucosyltransferase (E.C. 2.4.1.65) transfers L-fucose from GDP-fucose to OH-4 of the Glc pNAc residue in the disaccharide beta-D-Gal p-(1 --> 3)-beta-D-Glc pNAc-OR [R = (CH2)(8)COOMe] (1) to give the Lewis-A blood group determinant beta-D-Gal p-(1 --> 3)-[alpha-L-Fuc p-(1 --> 4)]-beta-D-Glc pNAc-OR. Five deoxy analogues of 1, as well as its N-propionyl derivative, were chemically synthesized and kinetically evaluated as both substrates and inhibitors for the enzyme from human milk. The unmodified acceptor 1 had K-m = 640 mu M with V-max set arbitrarily to 100. The 6-deoxy (K-m = 400 mu M, V-max = 90) and N-propionyl compounds (K-m = 330 mu M, V-max = 170) remained excellent substrates while the 4-deoxy compound was a very weak competitive inhibitor with K-i = 9 mM. Deoxygenation of OH-2' and OH-4' (of the Gal residue) in 1 had little effect on the activity. The OH-6 group of the Gal residue proved to be critical for recognition by the enzyme since substitution of this group with hydrogen led to an inactive compound. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00047-x
• 作为产物：
  描述：

  (Methoxycarbonyl)octyl 2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  O-α-L-鼠李糖吡喃糖基-（1进入3）-O-α-L-鼠李糖吡喃糖基-（1进入3）-2-乙酰氨基-2,6-的8-（甲氧羰基）辛基糖苷的合成双脱氧-D-吡喃葡萄糖; 铜绿假单胞菌Fisher免疫型5抗原模型。

  摘要：

  DOI：

  10.1016/s0008-6215(82)80027-x

文献信息

• The synthesis of monodeoxy derivatives of lacto-N-biose I and N-acetyl-lactosamine to serve as substrates for the differentiation of α-l-fucosyl transferases
  作者：Deveshwari P. Khare、Ole Hindsgaul、Raymond U. Lemieux

  DOI：10.1016/0008-6215(85)85204-6

  日期：1985.2

  β- d -Gal- and β- d -GlcNAc-α- l -fucosyl transferases. It is suggested that the enzymes accept the substrates in near their most favorable conformations and that the binding involves both polar and nonpolar interactions with topographical features near the hydroxyl group which undergoes substitution. It appears that, depending on the transferase, the recognition may or may not include both the sugar

  摘要β-d -Gal-（1→3）-4-deoxy-β-d-GlcNAcOR和β-d -Gal-（1→4）-3-deoxy-β-d-GlcNAcOR的化学合成，其中报告了R =（CH2）8COOMe和Me。此外，2-deoxy-β-d-Gal-（1→3）-β-d-GlcNAcO（ ）8COOMe和2-deoxy-β-d-Gal-（1→4）-β-d-GlcNAcO（合成CH 2）8 COOMe。关于这些化合物作为β-d-Gal-和β-d-GlcNAc-α-1-岩藻糖基转移酶的受体的行为，报道了来自其他实验室的初步结果。建议这些酶以其最有利的构象接受底物，并且该结合涉及极性和非极性相互作用，并具有在被取代的羟基附近的形貌特征。似乎取决于转移酶，识别可以包括或可以不包括两个糖单元。
• Fluoridolysis of 5,6-epoxy carbohydrates: application to the synthesis of 5-fluoro lactosamine and isolactosamine glycosides
  作者：Tara L. Hagena、James K. Coward

  DOI：10.1016/j.tetasy.2009.03.025

  日期：2009.5

  The synthesis of 6-selenophenyl derivatives of β-1,3 and β-1,4 disaccharides has been explored for the purpose of extending our epoxide fluoridolysis methodology to the synthesis of 5-fluoro analogues of N-acetyl isolactosamine (isoLacNAc, lacto-N-biose) and N-acetyl lactosamine (LacNAc) glycosides. Successful synthesis of the C-6 selenium-containing disaccharides was achieved via Lewis acid-mediated

  为了将我们的环氧化物荧光分解方法扩展到N-乙酰基异乳糖胺（isoLacNAc，乳酸酯-）的5-氟类似物的合成，已经探索了β-1,3和β-1,4二糖的6-硒苯基衍生物的合成。N-二糖）和N-乙酰基乳糖胺（LacNAc）糖苷。通过路易斯酸介导的供体和受体底物成功合成了含C-6硒的二糖，后者含有选择性保护的C-6羟基，可最终转化为所需的6-硒代苯二糖。相反，在多种条件下使用含硒受体底物不能产生所需的含硒二糖。将6-硒代苯衍生物氧化为相应的亚硒酸盐，然后进行热消除，得到环外烯烃，其被转化为5，6-环氧化物。环氧氟化反应产生所需的目标化合物，即1型和2型聚糖的5-氟β-辛基糖苷类似物。
• Synthesis of type 2 human blood-group antigenic determinants. The H, X, and Y haptens and variations of the H type 2 determinant as probes for the combining site of the lectin I of Ulex europaeus
  作者：Ole Hindsgaul、Thomas Norberg、Jacques Le Pendu、Raymond U. Lemieux

  DOI：10.1016/0008-6215(82)84034-2

  日期：1982.11

  Chemical syntheses of the human blood-group antigenic determinants derived from N-acetyllactosamine are described; namely, the 6-deoxy derivative, the 4'-epimer, and the 5 H type 2 [alpha LFuc(1 to 2)beta DGal-(1 to 4)beta DGlcNAc], X [beta DGal(1 to 4)[alpha LFuc(1 to 3)[beta DGlcNAc], and Y [alpha LFuc-(1 to 2)beta DGal(1 to 4)[alpha LFuc(1 to 3)]beta DGlcNAc] determinants as glycosides of 8-carboxymethyloctanol

  描述了衍生自N-乙酰基乳糖胺的人血型抗原决定簇的化学合成。即6-脱氧衍生物，4'-末端和5 H 2型[αLFuc（1至2）beta DGal-（1至4）beta DGlcNAc]，X [beta DGal（1至4）[ αLFuc（1至3）βDGlcNAc和Y [αLFuc-（1至2）βDGal（1至4）[αLFuc（1至3）]βDGlcNAc]决定基为8-羧甲基辛醇的糖苷。为了研究H 2决定簇与欧洲油菜的凝集素I的结合，还设计了专门改变H 2决定簇的亲水和疏水部分的结构。即6-脱氧衍生物，4'-末端和5“-正同源物。这些结构的使用，连同H 1型半抗原和H 1型和H 2型决定簇的N-去乙酰化形式一起，作为凝集素对O红细胞凝集的抑制剂，可以得出以下结论：H 2决定簇的结合是疏水性 结合涉及行列式分子的楔形部分，该楔形部分基本上是疏水性的，除了在楔形尖端处的5-羟甲基基团外，与O-5形成分子内氢
• Wessel, Hans-Peter; Iversen, Tommy; Bundle, David R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2247 - 2250
  作者：Wessel, Hans-Peter、Iversen, Tommy、Bundle, David R.

  DOI：——

  日期：——