methyl 2,3-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 69983-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: methyl 2,3-di-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；Methyl-2,2',3,3',6-penta-O-acetyl-β-laktosid；Gal2Ac3Ac(b1-4)b-Glc1Me2Ac3Ac6Ac；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 69983-01-3
• 化学式: C₂₃H₃₄O₁₆
• 分子量: 566.513
• InChiKey: WPQXHUVAUVQWGS-WGRYGTHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  209
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 Vibrio cholerae sialidase 、 4 A molecular sieve 、 sodium methylate 作用下， 以 四氢呋喃 、 重水 为溶剂， 反应 4.0h， 生成 甲基 4-O-BETA-D-半乳糖基-BETA-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Investigation of the Stability of Thiosialosides toward Hydrolysis by Sialidases Using NMR Spectroscopy

  摘要：

  H-1 NMR spectroscopy has been used to investigate whether the alpha(2-->6)-linked thiosialoside 3 and the alpha(2-->3)-linked thiosialoside 9 are hydrolyzed in the presence of Vibrio cholerae sialidase, Similarly, the hydrolysis of the O-ketosides Neu5Ac-2-O-alpha-(2-->3)-Gal beta Me (4) and the alpha-(2-->6)-sialyllactoside 7, representing natural alpha(2-->3)- and alpha(2-->6)-linked sialosides, respectively, was investigated. The results of the H-1 NMR experiments clearly demonstrate that the thiosialosides are not hydrolyzed by Vibrio cholerae sialidase, As expected, the O-sialosides are hydrolyzed to give N-acetyl-alpha-D-neuraminic acid as the first product of substrate cleavage.

  DOI：

  10.1021/ol990652w
• 作为产物：
  描述：

  methyl 2,2',3,3',6-penta-O-acetyl-4',6'-O-benzylidene-β-lactoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到methyl 2,3-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of tetrasaccharides as possible metastatic inhibitors

  摘要：

  The synthesis is reported of the possible metastatic inhibitors - methyl beta-D-galactopyranosyl-(1 --> 4)-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-(1 --> 6)-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranoside (11) and methyl beta-D-galactopyranosyl-(1 --> 4)-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 --> 6)-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranoside (14) - by procedures for regio- and stereo-selective coupling, reduction of azido groups, N-acetylation, and O-deacetylation. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00244-3

文献信息

• Chemical synthesis using enzymatically generated building units for construction of the human milk pentasaccharides sialyllacto-<i>N</i>-tetraose and sialyllacto-<i>N</i>-neotetraose epimer
  作者：Dirk Schmidt、Joachim Thiem

  DOI：10.3762/bjoc.6.18

  日期：——

  α,2-3- and α,2-6-sialylated lactosaminide precursor structures obtained by various enzymatic procedures could be used for glycosylations employing triflic acid/N-iodosuccinimide. Easily accessible selectively protected lactoside derivatives served as acceptor disaccharides to give the corresponding human milk pentasaccharides in good yields. These were characterized by spectroscopic means in the form of their peracetylated derivatives.

  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。
• CST-II’s recognition domain for acceptor substrates in α-(2→8)-sialylations
  作者：Wenling Li、Ping Zhang、Amir J. Zuccolo、Ruxiang Blake Zheng、Chang-Chun Ling

  DOI：10.1016/j.carres.2011.05.009

  日期：2011.9

  CST-II is a bacterial sialyltransferase known for its ability to perform alpha-(2 -> 8)-sialylations using GM(3) related trisaccharide substrates. Previously, we probed the enzyme's substrate specificity and developed an efficient synthesis for alpha-(2 -> 8)-oligosialosides, and we suggested that CST-II could have a very small substrate recognition domain. Here we report our full studies on CST-II's recognition feature for acceptor substrates. The current study further demonstrates the versatility of CST-II in preparing complex oligosaccharides that contain alpha-(2 -> 8)-oligosialyl moieties. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Sialylmimetics as Rotavirus Inhibitors
  作者：Ashmath Fazli、Susan J. Bradley、Milton J. Kiefel、Clare Jolly、Ian H. Holmes、Mark von Itzstein

  DOI：10.1021/jm0100887

  日期：2001.9.1

  Rotaviruses cause severe gastroenteritis in infants and are estimated to be responsible for over 600 000 deaths annually, primarily in developing countries. The development of potential inhibitors of this virus is therefore of great interest, particularly since the safety and efficacy of rotaviral vaccines has recently been questioned. This study describes the synthesis of a variety of compounds that can be considered as mimetics of N-acetylneuraminic acid thioglycosides and the subsequent in vitro biological evaluation of these sialylmimetics as inhibitors of rotaviral infection. Our results show that readily accessible carbohydrate-based compounds have the potential to act as inhibitors of rotaviral replication in vitro, presumably through inhibition of the rotaviral adhesion process.