methyl 2,3,4,6-tetra-O-propargyl-β-D-galactopyranoside | 870136-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-propargyl-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-methoxy-3,4,5-tris(prop-2-ynoxy)-6-(prop-2-ynoxymethyl)oxane
• CAS: 870136-60-0
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: DEESWTWQNHIQJZ-ICBNADEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴丙炔 、 甲基-Β-D-吡喃半乳糖苷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 以80%的产率得到methyl 2,3,4,6-tetra-O-propargyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120

  摘要：

  Water soluble and lectin-recognizable carbohydrate-centered glycoclusters were prepared efficiently by the Huisgen 1,3-cycloaddition reaction of methyl-2,3,4,6-tetra-O-propargyl beta-D-galactopyranoside with 2-azidoethyl glycosides of lactose and N-acetyllactosamine. Their binding by a plant lectin RCA(120) was examined by capillary affinity electrophoresis using fluorescence-labeled asialoglycans from human alpha 1-acid glycoprotein. The glycoclusters showed 400-fold stronger inhibitory effect than free lactose, manifesting strong multivalency effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.036

文献信息

• Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120
  作者：Yongjun Gao、Atsuko Eguchi、Kazuaki Kakehi、Yuan C. Lee

  DOI：10.1016/j.bmc.2005.06.036

  日期：2005.11

  Water soluble and lectin-recognizable carbohydrate-centered glycoclusters were prepared efficiently by the Huisgen 1,3-cycloaddition reaction of methyl-2,3,4,6-tetra-O-propargyl beta-D-galactopyranoside with 2-azidoethyl glycosides of lactose and N-acetyllactosamine. Their binding by a plant lectin RCA(120) was examined by capillary affinity electrophoresis using fluorescence-labeled asialoglycans from human alpha 1-acid glycoprotein. The glycoclusters showed 400-fold stronger inhibitory effect than free lactose, manifesting strong multivalency effect. (c) 2005 Elsevier Ltd. All rights reserved.