phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside | 5346-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 2^I,3^I,6^I,2^II,3^II,4^II,6^II-hepta-O-acetyl-1^I-thio-β-maltoside；phenyl 2,3,6-tri-O-acetyl-4-O-(2′,3′,4′,6′-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside；phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside；phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside；phenylthio 2,3,4,6-terta-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-triyl-O-acetyl-β-D-glucopyranoside；phenyl 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside；Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(b)-SPh；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 5346-81-6；28022-13-1；28022-14-2
• 化学式: C₃₂H₄₀O₁₇S
• 分子量: 728.725
• InChiKey: OJVHDCHVHOISBO-MMXCIQNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、133.32 Pa 条件下， 反应 2.0h， 生成 Phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Pearce, Alan James; Sollogoub, Matthieu; Mallet, Jean-Maurice, European Journal of Organic Chemistry, 1999, # 9, p. 2103 - 2117

  摘要：

  DOI：
• 作为产物：
  描述：

  麦芽糖 在 三氟化硼乙醚 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  在室温下使用1-氯-1,2-苯并恶唑醇3（1H）-一个高效TEMPO介导的糖伯醇氧化为糖醛酸

  摘要：

  使用1-氯-1,2-苯并恶恶唑3（1H）-one和TEMPO证明了各种糖伯醇被氧化为相应的糖醛酸。反应在室温下以良好至极好的收率进行。在温和的反应条件下，伯醇会比仲醇选择性地被氧化。

  DOI：

  10.1016/j.tetlet.2018.05.021

文献信息

• A Generalized Procedure for the One-Pot Preparation of Glycosyl Azides and Thioglycosides Directly from Unprotected Reducing Sugars under Phase-Transfer Reaction Conditions
  作者：Rishi Kumar、Pallavi Tiwari、Prakas R. Maulik、Anup K. Misra

  DOI：10.1002/ejoc.200500646

  日期：2006.1

  Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding

  过氧乙酰化糖基叠氮化物和硫代糖苷直接从未保护的还原糖通过通用的一锅法在相转移条件下原位生成过氧乙酰化糖基溴化物，以优异的收率制备。在糖基溴化物的异头中心完全反转形成立体选择性产物，为制备 1,2-反式糖基叠氮化物和硫代糖苷提供了一种通用的高产率方法。（© Wiley-VCH Verlag GmbH & Co. KGaA， 69451 德国魏因海姆，2006）
• Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
  作者：Tamashree Ghosh、Abhishek Santra、Anup Kumar Misra

  DOI：10.3762/bjoc.9.112

  日期：——

  A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.

  一系列的糖基半缩醛衍生物已经通过一锅两步反应序列（介导剂为Appel试剂（四溴化碳和三苯基膦））转化为硫代糖苷和糖基硫醇。通过原位生成的糖基溴化物与硫醇和碳硫代酸钠反应，选择性地形成了1,2-trans-硫代糖苷和β-糖基硫醇衍生物。反应条件相当简单，产率非常高。
• Glycosides and Salts Thereof
  申请人：Kuszmann Janos

  公开号：US20080249165A1

  公开（公告）日：2008-10-09

  The invention relates to new polysulfated glycosides of formula (I), the salts thereof formed with alkali metals or alkaline-earth metals, as well as the pharmaceutical compositions containing these compounds as active ingredients. Furthermore the invention provides a method of preventing, treating or alleviating the symptoms of acute and chronic inflammatory disorders of the airways of mammals—including asthma and asthma-related pathologies.

  该发明涉及公式（I）的新多硫酸基糖苷，以及与碱金属或碱土金属形成的盐，以及含有这些化合物作为活性成分的药物组合物。此外，该发明提供了一种预防、治疗或缓解哺乳动物呼吸道急性和慢性炎症性疾病症状的方法，包括哮喘和与哮喘相关的病理学。
• Elemental fluorine. Part 5. Reactions of 1,3-dithiolanes and thioglycosides with fluorine–iodine mixtures
  作者：Richard D. Chambers、Graham Sandford、Matthew E. Sparrowhawk、Malcolm J. Atherton

  DOI：10.1039/p19960001941

  日期：——

  1,3-Dithiolanes, prepared from diaryl ketones, react with elemental fluorine–iodine mixtures to give the corresponding difluoromethylene derivatives. Under the same conditions, thioglycosides give glycosyl fluorides in good yields. Reaction of 1,3-dithiolanes with fluorine in aqueous acetonitrile provides a remarkably mild method for efficient deprotection to the parent ketone.

  由二芳基酮制得的1,3-二硫杂环戊烷与元素氟-碘混合物反应生成相应的二氟亚甲基衍生物。在相同条件下，硫糖苷以良好的收率得到糖基氟化物。1,3-二硫杂环戊烷与氟在乙腈水溶液中的反应为有效脱保护母体酮提供了一种非常温和的方法。
• New Phenyl 6,4′-Substituted-1-Thio-β-Maltosides, Building Blocks for The Synthesis of Linear and Branched Malto-oligosaccharides
  作者：Mohammed Saddik Motawia、Kim Larsen、Carl Erik Olsen、Birger Lindberg Møller

  DOI：10.1055/s-2000-7601

  日期：——

  An efficient strategy to synthesize a number of new phenylthio-maltoside derivatives in yields from 55 to 95% is described. These derivatives can be used as suitable building blocks for stepwise synthesis of starch derived malto-oligosaccharides.

  描述了一种高效的策略，可以合成多种新的苯硫苷麦芽糖衍生物，其产率在55%到95%之间。这些衍生物可以作为分步合成淀粉衍生麦芽寡糖的合适构件。