methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside | 137119-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: Methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl-β-D-glucopyranoside
• CAS: 137119-40-5
• 化学式: C₂₀H₂₈O₁₁
• 分子量: 444.436
• InChiKey: GTNTZHZBKDWTBH-XPHMCCKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  156.53
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 乙酸肼 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-O-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis and biological evaluation of lactose-based sialylmimetics as inhibitors of rotaviral infection

  摘要：

  Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface sialoglycoconjugates, and is therefore an attractive target for potential therapeutic intervention. Since N-acetylneuraminic acid alpha(2,3)-linked to galactose is believed to be the minimum binding epitope of rotavirus to host cells, we report here our development of an efficient and flexible synthetic route to a range of lactose-based sialylmimetics of alpha(2,3)-linked thiosialosides. These compounds were biologically evaluated as inhibitors of rotaviral infection using an in vitro neutralisation assay. The results suggest that these lactose-based sialylmimetics are not inhibitors of the rhesus rotavirus strain; however, they do exhibit modest inhibition of the human (Wa) strain, presumably through inhibition of the rotaviral adhesion process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.057
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 甲基 4-O-BETA-D-半乳糖基-BETA-D-吡喃葡萄糖苷 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 以100%的产率得到methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Chemical synthesis using enzymatically generated building units for construction of the human milk pentasaccharides sialyllacto-N-tetraose and sialyllacto-N-neotetraose epimer

  摘要：

  通过各种酶法获得的α,2-3-和α,2-6-唾液酸化的乳糖氨基糖前体结构可用于利用三氟乙酸/N-碘代琥珀酰亚胺进行糖基化。易获得的有选择性保护的乳糖苷衍生物作为受体二糖，可高产率地给出相应的人乳五糖。这些通过光谱手段以过乙酰化衍生物的形式进行表征。

  DOI：

  10.3762/bjoc.6.18

文献信息

• Synthesis and structure–activity relationships of di- and trisaccharide inhibitors for Shiga-like toxin Type 1
  作者：Pavel I. Kitov、David R. Bundle

  DOI：10.1039/b009685g

  日期：——

  The syntheses of galabiose and Pk-trisaccharide analogues in which selected hydroxy groups are replaced by O-methyl, amino deoxy, acetamido deoxy, and carboxyalkyl groups are reported. The ability of these inhibitors to block E. coli verotoxin 1 binding to its mammalian cell-surface receptor are evaluated by a solid-phase competition assay. The synthesis of a biotinylated glycoconjugate for this assay

  合成的半乳糖和P k-三糖类似物，其中选定的羟基被O-甲基取代，氨基 脱氧 乙酰氨基报道了脱氧和羧基烷基。这些的能力抑制剂通过固相竞争测定法评估阻断大肠杆菌维毒素1与其哺乳动物细胞表面受体的结合的方法。描述了用于该测定法的生物素化的糖缀合物的合成，其中构建了P k-三糖系链衍生物70并将其共价附接到牛血清白蛋白上，随后是生物素化。半乳糖衍生物4和5含有羧甲基β-半乳糖残基的O --2处的羧基或羧基乙基取代基显示出15-20倍的活性增加甲基糖苷半乳糖。对于相应的羧甲基取代的P k-三糖类似物13，未观察到这种增强的活性。通过与P k-三糖类似物复合的Verotoxin 1的晶体结构合理化抑制数据，并为二聚体的设计提供了见识抑制剂可以利用毒素B亚基的独特结合位点分布。该讨论提供了由有序人扮演的重要角色的另一个示例。水 糖中的分子蛋白质 复合体。
• Thio and epidithio derivatives of methyl β-lactoside
  作者：Mezher A. Ali、Leslie Hough、Anthony C. Richardson

  DOI：10.1016/0008-6215(92)84168-r

  日期：1992.9

  3′,6′-anhydro-6-bromo-6-deoxy derivative, from which 6-thio derivatives were prepared, and methyl 3′,4′-O-isopropylidene-β-lactoside gave the 6,6′-dibromo-6,6′-dideoxy derivative. A dibromide was prepared also from methyl 4′,6′-O-benzylidene-β-lactoside by bromination with Ph3P-CBr4, acetylation, and then treatment with N-bromosuccinimide. Various 6,6′-dithio derivatives were prepared from the 6,6′-dibromide

  摘要用三苯基膦-四溴化碳在吡啶中处理甲基β-乳糖苷，得到3'，6'-脱水-6-溴-6-脱氧衍生物，制备了6-硫代衍生物，甲基3'，4'- O-异亚丙基-β-乳糖苷得到6,6'-二溴-6,6'-二脱氧衍生物。也由甲基4′，6′-O-亚苄基-β-乳糖苷通过用Ph 3 P-CBr 4溴化，乙酰化，然后用N-溴代琥珀酰亚胺处理来制备二溴化物。通过亲核取代反应从6,6'-二溴化物制备了各种6,6'-二硫代衍生物。6，6′-二溴化物与硫脲的反应产生6，6′-表二硫代衍生物，并与三硫代碳酸钾形成桥连的6，6′-三硫代碳酸酯。对6,6'-二溴衍生物进行选择性亲核取代，得到各种6'-溴-6-硫代衍生物。同样地，用叠氮化物首先形成6-叠氮化物，然后形成6,6'-二叠氮化物和消除的产物6-叠氮基-5'-烯。阮内镍介导的各种6,6'-二硫代衍生物的脱硫得到甲基6,6'-二脱氧-β-乳糖苷，并且可以实现6'-溴-6
• Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl β-lactoside as ligands for the Ricinus communis lectins
  作者：Paloma Fernández、Jesús Jiménez-Berbero、Manuel Martín-Lomas

  DOI：10.1016/0008-6215(94)84243-4

  日期：1994.2

  The synthesis of all the possible monomethyl ethers of methyl beta-lactoside (1) has been performed from 1 in a straightforward way, making use of the different reactivity of the hydroxyl groups in alkylation and stannylation reactions. In addition, the deoxyfluoro derivatives of 1 at positions, 6,3',4',epi-4', and 6' have been prepared by reaction of the appropriate substrates with diethylaminosulfur

  甲基β-内酯（1）的所有可能的单甲基醚的合成已从1直接进行，利用了烷基化和甲锡烷基化反应中羟基的不同反应性。另外，通过适当的底物与二乙基氨基三氟化硫或氟化四丁基铵的反应制备了在6,3'，4'，epi-4'和6'位置的1的脱氧氟衍生物。最后，还制备了1的6-脱氧碘和6'-溴脱氧氧基类似物。
• Carbohydrate−Carbohydrate Recognition Between Lewis X Blood Group Antigens, Mediated by Calcium Ions
  作者：Christian Gege、Armin Geyer、Richard R. Schmidt

  DOI：10.1002/1099-0690(200208)2002:15<2475::aid-ejoc2475>3.0.co;2-m

  日期：2002.8
• Nucleoglycoconjugates: Design and Synthesis of a New Class of DNA–Carbohydrate Conjugates
  作者：Terry L. Sheppard、Chi-Huey Wong、Gerald F. Joyce

  DOI：10.1002/1521-3773(20001016)39:20<3660::aid-anie3660>3.3.co;2-c

  日期：2000.10.16