methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside | 91852-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside；Methyl-3,6-di-O-acetyl-2-azido-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosid
• CAS: 91852-13-0
• 化学式: C₂₅H₃₅N₃O₁₆
• 分子量: 633.563
• InChiKey: LOURSLPOOXIACA-YOJZCWELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.0
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  243.48
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到methyl O-β-D-galactopyranosyl-(1-4)-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Wong, Ting C.; Lemieux, Raymond U., Canadian Journal of Chemistry, 1984, vol. 62, p. 1207 - 1213

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸酐 、 methyl O-β-D-galactopyranosyl-(1-4)-2-azido-2-deoxy-β-D-glucopyranoside 在 吡啶 作用下， 生成 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Lewissäure-katalysierte合成二糖和三糖序列的O-和N-糖蛋白。冯·冯·三甲基甲硅烷基三氟甲磺酸

  摘要：

  摘要在三甲基甲硅烷基三氟甲磺酸酯作为路易斯酸催化剂的存在下，β-乙酸酯作为糖基供体并与邻近基团反应，与低反应性的糖的仲羟基反应，从而以高收率得到β-糖苷键合的二糖和寡糖。该反应的两种化合物的保护基必须在酸性条件下是稳定的。因此，1,2,3,4,6-戊基-O-乙酰基-β-d-吡喃半乳糖与甲基2-叠氮基-4,6-二-O-苯甲酰基-2-脱氧-β-d-的反应半乳糖吡喃糖苷以83％的收率得到甲基2-叠氮基-2,6-二-O-苯甲酰基-2-脱氧-3-O-（2,3,4,6-四-O-乙酰基-β-d- （吡喃半乳糖）-β-d-吡喃半乳糖苷是有用的构建单元。比较了路易斯酸催化和Koenigs-Knorr条件下的糖苷反应。

  DOI：

  10.1016/0008-6215(84)85005-3

文献信息

• Characterization of inhibitory activities and binding mode of synthetic 6′-modified methyl N-acetyl-β-lactosaminide toward rat liver CMP-d-Neu5Ac: d-galactoside-(2 → 6)-α-d-sialyltransferase
  作者：Yasuhiro Kajihara、Hisashi Kodama、Tomio Wakabayashi、Ken-ichi Sato、Hironobu Hashimoto

  DOI：10.1016/0008-6215(93)84251-z

  日期：1993.9

  6'-Deoxy (12), 6'-thio (13), and 6'-O-tetrahydropyranosyl (14) analogues of methyl N-acetyl-beta-lactosaminide (3), were synthesized from lactose. NOE experiments proved that they adopt the same conformation as that of 3. Inhibition studies using these synthetic analogues, including the disulfide dimer 15, toward (2 --> 6)-alpha-sialyltransferase (EC 2.4.99.1) revealed that the 6'-deoxy analogue 12 had remarkable inhibitory activity as the first acceptor-analogue inhibitor for this enzyme. It is noteworthy that the disulfide 15 also behaves as an inhibitor. The results indicated that chemical modification at the 6'-position of 3 did not cause much decrease in the binding affinity to the sialyltransferase. Further, a novel possibility that the acceptor and the acceptor-analogue inhibitor can bind simultaneously to the sialyltransferase was proposed based on the inhibition studies with 12 and CMP.