2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide
• 英文别名: 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide；(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-bromotetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate；acetobromo-α-D-sophorose；acetobromosophorose；O³,O⁴,O⁶-triacetyl-O²-(tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl bromide；α-acetobromosophorose；Glc2Ac3Ac4Ac6Ac(b1-2)a-Glc1Br3Ac4Ac6Ac；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate
• 化学式: C₂₆H₃₅BrO₁₇
• 分子量: 699.458
• InChiKey: DNCXZNISOVOMCH-VRECAULFSA-N

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：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide 在 sodium methylate 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 α-sophoroside
  参考文献：
  名称：

  甜菊糖的全合成

  摘要：

  通过应用糖苷的立体选择方法将甜菊醇2转化为甜菊糖苷1。

  DOI：

  10.1016/0040-4020(80)80136-0
• 作为产物：
  描述：

  methyl (Z,17S)-17-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoctadec-9-enoate 在 palladium on activated charcoal 、 氢溴酸 、 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  从槐糖脂到天然产物合成

  摘要：

  槐糖脂（SL）是二糖槐糖的一个容易获得的，可扩展的来源：按照四个步骤的顺序，将发酵液中的粗产物转化为关键的二糖供体7，这些供体进一步被用于天然产物Ebracteatoside C的合成中，zyzybeoside I和苯乙基糖苷。Zizybeoside I和苯乙基糖苷的糖苷配基是市售的简单伯醇，而Ebrateatoside C的合成则需要仲烯丙醇（R）-6-羟基辛基-7-烯基乙酸酯。对映体纯的仲醇通过醇脱氢酶催化的还原为关键步骤分两步合成。

  DOI：

  10.1002/adsc.201101005

文献信息

• 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
• 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。
• Biomimetic synthesis of nudicaulins I and II, yellow pigments from the Iceland poppy<i>Papaver nudicaule</i>
  作者：Rory Devlin、Jonathan Sperry

  DOI：10.1039/c9cc07943b

  日期：——

  Indole and the anthocyanin orientalin proceed through a unique cascade sequence that leads to nudicaulins I and II in 92% yield. This biomimetic synthesis confirms the biosynthesis proposal for these structurally unprecedented flavoalkaloids that play a key role in the colour range displayed by the Iceland poppy.

  吲哚和花色苷东方香精通过独特的级联序列进行操作，从而以92％的收率得到了芥子油苷I和II。这种仿生合成证实了这些结构上前所未有的黄素生物碱的生物合成提议，这些黄素生物碱在冰岛罂粟所显示的颜色范围中起关键作用。
• Novel Process for the Preparation of Rebaudioside D and Other Related Naturally Occurring Sweetners
  申请人：SU ZHOU JING HONG BIOTECH CO., LTD.

  公开号：US20140296499A1

  公开（公告）日：2014-10-02

  A novel process for preparation of Rebaudioside D (RD), and other related naturally occurring sweeteners is provided. RD is a natural sweetening agent which can decrease the bitter aftertaste of steviol glycosides. The said process is suitable for commercial manufacturing by using readily available natural products and nontoxic reagents.

  提供了一种制备雷巴甙D（RD）和其他相关天然甜味剂的新工艺。RD是一种天然甜味剂，可以减少史蒂维奥甙的苦涩余味。该工艺适用于商业生产，使用易获得的天然产品和无毒试剂。
• Synthesis of linear oligosaccharides: l-glycero-α-d-manno-heptopyranosyl derivatives of allyl α-glycosides of d-glucose, kojibiose, and 3-O-α-kojibiosyl-d-glucose, substrates for synthetic antigens
  作者：Sergey A. Nepogod'ev、Leon V. Backinowski、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/0008-6215(94)84242-6

  日期：1994.2

  Synthesis of the title oligosaccharides was performed with the use of peracetylated L-glycero-beta-D-manno-heptosyl trichloroacetimidate as the heptosyl donor and (oligo)glucosyl accepters bearing acyl and acetal protecting groups.