hepta-O-acetyl-α-gentiobiosyl bromide | 14187-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hepta-O-acetyl-α-gentiobiosyl bromide
• 英文别名: hepta-O-acetyl-α-D-gentiobiosyl bromide；acetobromogentiobiose；α-acetobromogentiobiose；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 14187-83-8
• 化学式: C₂₆H₃₅BrO₁₇
• 分子量: 699.458
• InChiKey: QLNKYWGJSVLWHY-DEZPWFOKSA-N

物化性质

• 熔点：
  131-133.5 °C
• 沸点：
  644.7±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  hepta-O-acetyl-α-gentiobiosyl bromide 在 palladium on activated charcoal calcium sulfate 、 氢气 、 碘 、 sodium methylate 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 为溶剂， -20.0~20.0 ℃ 、344.74 kPa 条件下， 生成 3-O-(β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl)oleanolic acid
  参考文献：
  名称：

  Synthesis and Haemolytic Activity of Randianin Isomers

  摘要：

  DOI：

  10.1007/pl00010270
• 作为产物：
  描述：

  1,2,3,4-四-O-乙酰基-β-D-葡萄吡喃糖 在 乙酰溴 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 hepta-O-acetyl-α-gentiobiosyl bromide
  参考文献：
  名称：

  Gentiobiosylation of β-Resorcylic Acid Esters and Lactones: First Synthesis and Characterization of Zearalenone-14-β,d-Gentiobioside

  摘要：

  The development of an optimized protocol for the gentiobiosylation of beta-resorcylic acid esters and lactones (beta-RAL) is presented. Different gentiobiosyl donors were prepared and used for regioselective and diastereoselective glycosylation affording a reliable synthetic strategy towards this class of natural product glycosides. The improved procedure was finally used for the preparation of the masked Fusarium mycotoxin zearalenone-14-beta,D-gentiobioside.

  DOI：

  10.1055/s-0033-1339338

文献信息

• Glycosylation of acids under phase transfer conditions. Partial synthesis of saponins
  作者：Christophe Bliard、Georges Massiot、Serge Nazabadioko

  DOI：10.1016/0040-4039(94)88088-3

  日期：1994.8

  β-D-glycosyl esters are prepared in high yields by reaction of various carboxylic acids and acetobromosugars. The reaction uses potassium carbonate under phase tranfer conditions. Deacetylation affords the β-D-glycosyl carboxylates.

  通过各种羧酸与乙酰溴糖的反应，可以高产率制备β-D-糖基酯。反应在相转移条件下使用碳酸钾。脱乙酰基得到β-D-糖基羧酸盐。
• Synthese und1H-NMR-Studie der vier unverzweigten peracetylierten ?-D-Glucopyranosyl-?-gentiobiosen
  作者：Martin Rychener、Peter Bigler、Hanspeter Pfander

  DOI：10.1002/hlca.19840670204

  日期：1984.3.14

  Synthesis and 1H-NMR Study of the Four Unbranched Peracetyl-β-D-glucopyranosyl-β-gentiobioses

  四种直链过乙酰基-β-D-吡喃葡萄糖基-β-龙胆素酶的合成及1 H-NMR研究
• 3-nitropropyl glycosides ofAstragalus miser var.serotinus
  作者：Melissa Long、Michael Benn、Walter Majak、Ruth McDiarmid

  DOI：10.1016/0031-9422(91)83063-q

  日期：1992.1

  Abstract On the basis of spectroscopic and chemical evidence, 3-nitropropyl β- d -cellobioside was identified among the toxic glycosides produced by Astragalus miser var. serotinus and its structure confirmed by synthesis, as was that of the β- d -gentiobioside previously isolated from this plant.

  摘要 根据光谱学和化学证据，在黄芪产生的有毒糖苷中鉴定出3-硝基丙基β-d-纤维二糖苷。serotinus 及其结构通过合成证实，如先前从该植物中分离的 β-d-龙胆二糖苷。
• Stereospecific Synthesis of 1,2-<i>trans</i>-1-Phenylthio-β-D-Disaccharides Under Phase Transfer Catalysis
  作者：François D. Tropper、Fredrik O. Andersson、Chantal Grand-Maître、René Roy

  DOI：10.1055/s-1991-26559

  日期：——

  Peracetylated α-glycobiosyl bromides 1-5 derived from commercially available disaccharides, were transformed with complete anomeric stereocontrol into phenyl 1,2-trans-1-thio-β-D-glycobiosides 6-10 by nucleophilic displacement under phase transfer catalyzed glycosidation in 77-92% yields. The reaction proceed rapidly for most bromides in dichloromethane, but failed under similar conditions, to provide complete conversion of the melibiosyl bromide 4 into the S-phenyl thioglycoside 9. Nevertheless, the reaction gave good results when performed in toluene or ethyl acetate.

  商业上可获得的二糖衍生的过乙酰化α-糖基溴化物1-5，在相转移催化的糖苷化条件下通过亲核取代反应，以77-92%的收率完全立体选择性地转化为苯基1,2-反式-1-硫代-β-D-糖苷6-10。对于大多数溴化物，反应在二氯甲烷中能快速进行，但在相似条件下，无法将美力糖基溴化物4完全转化为S-苯基硫代糖苷9。然而，当在甲苯或乙酸乙酯中进行反应时，能获得良好的结果。
• Synthesis and Hemolytic Properties of Glycyrrhetic Acid Glycosides
  作者：Nisar Ullah、Werner Seebacher、Robert Weis、Johann Jurenitsch、Katharina Rauchensteiner、Ernst Haslinger

  DOI：10.1007/s007060050026

  日期：——

   The synthesis of monodesmosidic glycyrrhetic acid disaccharides via its diphenylmethyl ester is described. Their hemolytic activity is lower as compared to the corresponding oleanolic aciddisaccharides. The influence of the structure of the aglycon on the hemolytic activity is discussed.

  描述了 通过  其二苯基甲基酯合成单去糖甘草次酸二糖 。与相应的齐墩果酸二糖相比，它们的溶血活性较低。讨论了糖苷配基的结构对溶血活性的影响。