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 | 56865-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 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
• 中文别名: 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
• 英文名称: methyl 4',6'-O-benzylidene-β-lactoside
• 英文别名: (4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 56865-31-7
• 化学式: C₂₀H₂₈O₁₁
• 分子量: 444.436
• InChiKey: GTNTZHZBKDWTBH-NYOUCEBBSA-N

物化性质

• 沸点：
  702.8±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  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 在 palladium on activated charcoal 咪唑 、 氢气 、 碘 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl 6-deoxy-β-lactoside
  参考文献：
  名称：

  蓖麻凝集素对合成甲基β-乳糖苷类似物的分子识别研究。

  摘要：

  已经合成了甲基β-乳糖苷的2-，3-，6-，2'-，3'-，4'-和6'-脱氧衍生物和3-O-甲基衍生物，并且它们与半乳糖结合研究了来自蓖麻的特异性凝集素（RCA-120）。结果表明，β-D-吡喃半乳糖部分的HO-3、4、6是关键的极性基团。与紧密相关的蓖麻毒素凝集素RCA-60的主要区别在于D-吡喃葡萄糖部分的HO-6，这似乎有助于碳水化合物与RCA-60的结合而不与RCA-120的结合。

  DOI：

  10.1016/0008-6215(92)80055-6
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 IR resin (H+) 、 camphor-10-sulfonic acid 、 sodium methylate 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 51.0h， 生成 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
  参考文献：
  名称：

  An efficient glycosylation reaction for the synthesis of asialo GM2 analogues

  摘要：

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.008

文献信息

• 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.
• Synthesis of tetrasaccharides as possible metastatic inhibitors
  作者：Xiao Xiang Zhu、Ping Yu Ding、Meng Shen Cai

  DOI：10.1016/s0008-6215(96)00244-3

  日期：1996.12

  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.
• 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.