methyl 4,6-O-(phenylmethylene)-3-O-<(trifluoromethyl)sulfonyl>-β-D-galactopyranoside | 129217-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-(phenylmethylene)-3-O-<(trifluoromethyl)sulfonyl>-β-D-galactopyranoside
• 英文别名: methyl 4,6-O-benzylidene-3-O-[(trifluoromethyl)sulfonyl]-β-D-galactopyranoside；methyl 4,6-O-(phenylmethylene)-3-O-[(trifluoromethyl)sulfonyl]-β-D-galactopyranoside
• CAS: 129217-27-2
• 化学式: C₁₅H₁₇F₃O₈S
• 分子量: 414.356
• InChiKey: QSOYMJYPDZMKRA-IKKURHKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-(phenylmethylene)-3-O-<(trifluoromethyl)sulfonyl>-β-D-galactopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以57%的产率得到Methyl 2-deoxy-2-C-formyl-4,6-O-(phenylmethylene)-β-D-xylo(lyxo)furanoside
  参考文献：
  名称：

  Reactions of some pyranoside diol monotriflates with nucleophiles and bases

  摘要：

  Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and ''epimerized'' pyranosides, particularly where a fused acetal ring inhibits ring contraction. Among the substrates examined (1, 2,3,4,35), only 4 shows a strong tendency to give ring-contracted products. The reaction of 1-3 with more basic nucleophiles (F-, t-BuO-) leads to the anhydrosugars 8, 25, and 26, respectively. The S(N)2 reaction of 35 with tetra-n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.

  DOI：

  10.1021/jo00052a058
• 作为产物：
  描述：

  三氟甲磺酸酐 、 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 在 二正丁基氧化锡 、 4 A molecular sieve 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.5h， 以70%的产率得到methyl 4,6-O-(phenylmethylene)-3-O-<(trifluoromethyl)sulfonyl>-β-D-galactopyranoside
  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

文献信息

• Amino alcohol and amino sugar synthesis by benzoylcarbamate cyclization
  作者：Spencer Knapp、Paivi J. Kukkola、Shashi Sharma、T. G. Murali Dhar、Andrew B. J. Naughton

  DOI：10.1021/jo00309a013

  日期：1990.10
• Synthesis of 3-azido-3-deoxy-β-d-galactopyranosides
  作者：Christopher T. Öberg、Ann-Louise Noresson、Tamara Delaine、Amaia Larumbe、Johan Tejler、Henrik von Wachenfeldt、Ulf J. Nilsson

  DOI：10.1016/j.carres.2009.05.005

  日期：2009.7

  Three efficient routes to 3-azido-3-deoxy-beta-D-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-D-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-D-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-D-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.