2,3,4-tri-O-benzyl-D-xylono-1,5-lactone | 153751-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-tri-O-benzyl-D-xylono-1,5-lactone
• 英文别名: 2,3,4-tri-O-benzyl-D-xylonolactone；xylonolacetone；(3R,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-one
• CAS: 153751-46-3
• 化学式: C₂₆H₂₆O₅
• 分子量: 418.489
• InChiKey: FXZASCOMEUCXNB-DSNGMDLFSA-N

物化性质

• 沸点：
  582.1±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-D-xylono-1,5-lactone 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 23.5h， 生成 4-fluoro-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]-1H-indole
  参考文献：
  名称：

  NOVEL GLYCOSIDE COMPOUNDS

  摘要：

  式（I）的化合物：其中X、Y和Z在此处定义。还披露了与这些化合物相关的药物组合物和治疗方法。

  公开号：

  US20130157970A1
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-D-xylopyranoside 在 硫酸 、 碘 、 potassium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 2,3,4-tri-O-benzyl-D-xylono-1,5-lactone
  参考文献：
  名称：

  Ring-opened 4-hydroxy-δ-valerolactone subunit as a key structural fragment of polyesters that degrade without acid formation

  摘要：

  Random copolymers of C-caprolactone with O-benzyl-protected 4-hydroxy- or 2,4-dihydroxy-delta-valerolactone after hydrogenation form gamma-hydroxy functionalized polyesters that degrade via the cyclization to gamma-butyrolactone fragments without carboxylic acid formation.

  DOI：

  10.1016/j.mencom.2018.11.022

文献信息

• Total Synthesis of Everninomicin 13,384-1—Part 2: Synthesis of the FGHA2 Fragment
  作者：K. C. Nicolaou、Helen J. Mitchell、Konstantina C. Fylaktakidou、Rosa Maria Rodríguez、Hideo Suzuki

  DOI：10.1002/1521-3765(20000901)6:17<3116::aid-chem3116>3.0.co;2-8

  日期：2000.9.1

  The stereoselective synthesis of everninomicin's 13,384-1 (1) FGHA2 fragment (2) in a suitable form for incorporation into the final target (1) is described. The construction of the FG 1,1'-disaccharide linkage relied on a new method based on tin-acetal chemistry, while for the GH orthoester bridge, a number of approaches were explored. Final success for the latter construction came when a novel 1

  描述了以合适的形式结合到最终靶标（1）中的everninomicin's 13,384-1（1）FGHA2片段（2）的立体选择性合成。FG 1,1'-二糖键的构建依赖于基于锡-缩醛化学的新方法，而对于GH原酸酯桥，则探索了许多方法。后一种结构的最终成功是通过将新的1,2-苯基硒代迁移反应应用于环G和H偶联，随后是乙烯酮缩醛和原酸酯的形成。
• Metal-free oxidative lactonization of carbohydrates using molecular iodine
  作者：Maxime B. Fusaro、Vincent Chagnault、Solen Josse、Denis Postel

  DOI：10.1016/j.tet.2013.05.021

  日期：2013.7

  We describe herein the oxidative lactonization of fully or partially protected carbohydrates using molecular iodine. Oxidation of aldose hemiacetals is generally carried out by classical procedures, which are rarely chemo or regioselective. We recently reported an optimized methodology for the oxidative amidation of aldose with functionalized amines and we found molecular iodine as a good selective oxidant

  我们在本文中描述了使用分子碘对全部或部分保护的碳水化合物的氧化内酯化。醛糖半缩醛的氧化通常通过经典方法进行，该方法很少具有化学或区域选择性作用。我们最近报道了一种优化的方法，用于醛糖与功能化胺的氧化酰胺化反应，我们发现分子碘是一种很好的选择性氧化剂。该性质已被其他研究小组观察到，但从未研究过碳水化合物的反应性范围。这种方法的主要优点在于操作简便，无需使用复杂的试剂和程序。
• Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
  作者：Grzegorz Witkowski、Mykhaylo A. Potopnyk、Karolina Tiara、Anna Osuch-Kwiatkowska、Sławomir Jarosz

  DOI：10.3390/molecules25153357

  日期：——

  2,3,4-Tri-O-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure.

  2,3,4-三-O-苄基-D-吡喃木糖用作制备相应三烯的起始材料，三烯顺利环化为多羟基化的海茚，作为单一的非对映异构体。由 D-葡萄糖制备的类似三烯即使在高压下也不发生任何环化。
• Metal-free oxidative esterification of benzylated monosaccharides
  作者：Tchambaga Camara、Abed Bil、Vincent Chagnault

  DOI：10.1016/j.carres.2018.04.003

  日期：2018.6

  Methyl glyconates have been attracting considerable attention as intermediates for the preparation of aryl C-glycosides, polyphenolic products, aliphatic polyesters, SGLT2 inhibitors, antibiotics etc … In view of the interest in those compounds, we report herein our work on the synthesis of methyl glyconates using an oxidative esterification carried out by molecular iodine. This reaction is catalyzed

  糖基乙酸甲酯作为制备芳基C-糖苷，多酚产品，脂族聚酯，SGLT2抑制剂，抗生素等的中间体已引起了相当大的关注。鉴于对这些化合物的兴趣，我们在此报告我们在合成糖基乙酸甲酯方面的工作。使用由分子碘进行的氧化酯化。该反应由无毒的K4Fe（CN）6催化，该K4Fe（CN）6向反应混合物中释放少量氰化物离子。已成功测试了包含半缩醛官能团的四种苄基化碳水化合物。
• Enzymic .beta.-Galactosidation of Modified Monosaccharides: Study of the Enzyme Selectivity for the Acceptor and Its Application to the Synthesis of Disaccharides
  作者：Rosa Lopez、Alfonso Fernandez-Mayoralas

  DOI：10.1021/jo00083a013

  日期：1994.2

  The selectivity of the E. coli beta-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide accceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.