methyl 2,2',3,3',6-penta-O-acetyl-4',6'-O-benzylidene-β-lactoside | 69983-00-2

• 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 2,2',3,3',6-penta-O-acetyl-4',6'-O-benzylidene-β-lactoside
• 英文别名: methyl 2,3-di-O-acetyl-4,6-O-beznzylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；methyl 4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；Methyl-2,2',3,3',6-penta-O-acetyl-4',6'-O-benzyliden-β-lactosid；[(2R,3R,4S,5R,6R)-3-[[(4aR,6S,7R,8S,8aS)-7,8-diacetyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-4,5-diacetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 69983-00-2
• 化学式: C₃₀H₃₈O₁₆
• 分子量: 654.622
• InChiKey: YUUHVPVFGMLYIY-RIKZJYHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲基 4-O-[4,6-O-(苯基亚甲基)-beta-D-半乳糖基]-beta-D-吡喃葡萄糖苷 、 乙酸酐 在 吡啶 作用下， 反应 16.0h， 生成 methyl 2,2',3,3',6-penta-O-acetyl-4',6'-O-benzylidene-β-lactoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Sialylmimetics as Rotavirus Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm0100887

文献信息

• Carbohydrate-derived surfactants: synthesis and phase behaviour of methyl 4′ 6′-di-O-alkyl-β-lactosides
  作者：Virginie Langlois、J. Michael Williams

  DOI：10.1039/p19940002103

  日期：——

  In order to study the physical properties of lactose-derived surfactants. methyl 4',6'-di-O-hexyl-beta-lactoside and methyl 4',6'-di-O-octyl-beta-lactoside were prepared. The 4',6'-O-isopropylidene ketal was used as a temporary protecting group in the key intermediate. The 3',4'-O-benzylidene acetal was identified as a minor by-product in the preparation of methyl 4',6'-O-benzylidene-beta-lactoside by acid-catalysed transacetalation. The phase behaviour of these derivatives is reported.