allyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside | 1357296-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside
• CAS: 1357296-81-1
• 化学式: C₃₀H₂₈O₉
• 分子量: 532.547
• InChiKey: IREUAKAPJGOFFS-OFBRLNSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 三氟甲磺酸三甲基硅酯 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Development of a fluorescent probe for the study of the sponge-derived simplexide immunological properties

  摘要：

  Simplexide is a glycolipid of marine origin, endowed with immunological properties, composed of a long chain secondary alcohol glycosylated by an alpha-D-glucosyl-(1 -> 4)-beta-D-galactosyl disaccharide residue. Herein we describe the preparation of a fluorescent derivative of simplexide, labeled at position 6 of the distal glucose with a dansyl group, as a probe for future studies on the mechanism by which simplexide affects the immune system. Fluorescent simplexide was prepared from a 6 ''-amino functionalized compound, which in turn was obtained through a highly efficient glycosylation between the preformed activated disaccharide and the long chain secondary alcohol 18-pentatriacontanol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.11.017
• 作为产物：
  描述：

  allyl β-D-galactopyranoside 、 苯甲酰氯 在 吡啶 作用下， 以31%的产率得到allyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Potential use of synthetic α-galactosyl-containing glycotopes of the parasite Trypanosoma cruzi as diagnostic antigens for Chagas disease

  摘要：

  合成糖阵列含有与寄生虫克氏锥虫粘蛋白 O 聚糖相关的非还原性 α-吡喃半乳糖基部分，通过化学发光酶联免疫吸附测定对慢性恰加斯病患者的血清进行评估。我们的数据显示二糖 Galα(1,3)Galβ 作为免疫显性糖表位，最终可能用作恰加斯病的诊断抗原。

  DOI：

  10.1039/c3ob40887f

文献信息

• Sialylation with systematically protected allyl galactoside acceptors using sialyl phosphate donors
  作者：Kenta Kurimoto、Hatsuo Yamamura、Atsushi Miyagawa

  DOI：10.1016/j.tetlet.2016.02.052

  日期：2016.3

  Various N-protected sialyl donors were synthesized and utilized in sialylation to investigate the reactivity and stereoselectivity of sialyl phosphate donors. Furthermore, in order to understand the effects of protecting groups and hydroxyl group positions on galactosyl acceptors, the sialylation efficiencies of all of the hydroxy groups on galactoses, which were protected with benzyl or benzoyl groups, were investigated. Consequently, the sialylation of N-acetyl-5-N,4-O-oxazolidinone-protected sialyl phosphate donors with allyl galactosides was accomplished and gave the GM4 regioisomers. (C) 2016 Elsevier Ltd. All rights reserved.