2,5-anhydro-3,4-di-O-benzyl-D-mannitol | 222555-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4-di-O-benzyl-D-mannitol
• 英文别名: 3,4-di-O-benzyl-2,5-anhydro-D-mannitol；[(2R,3R,4R,5R)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol
• CAS: 222555-96-6
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GCCFBDFJFARWGD-UAFMIMERSA-N

物化性质

• 熔点：
  76-78 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  511.5±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4-di-O-benzyl-D-mannitol 在 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose
  参考文献：
  名称：

  First synthesis of methyl α-C-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside: the C-disaccharide segment of motif C of Mycobacterium tuberculosis

  摘要：

  The synthesis of C-analogue of the disaccharide 2 alpha-araf-(1-->5)-ara present in motif C of the arabino-galactan portion of Mycobacterium tuberculosis, has been described. The critical C-C bond formation reaction to couple both the furanosyl residues has been accomplished through nitro-aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01760-4
• 作为产物：
  描述：

  D-arabinose diethyl dithioacetal 在 过氧乙酸 、 硫酸 、 三氟化硼乙醚 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 potassium bromide 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 22.5h， 生成 2,5-anhydro-3,4-di-O-benzyl-D-mannitol
  参考文献：
  名称：

  Preparation of 2,5-Anhydrohexitols (Part I). Silicon-Directed Stereocontrolled Cyclization

  摘要：

  Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3. Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.

  DOI：

  10.1080/07328309908543989

文献信息

• Total Synthesis of an Antitumor Agent, Mucocin, Based on the “Chiron Approach”
  作者：Shunya Takahashi、Tadashi Nakata

  DOI：10.1021/jo020211h

  日期：2002.8.1

  aldehyde 4 in the presence of CeCl(3). Synthesis of the lactone 3 relied on a novel approach by taking advantage of a radical cyclization of acyclic selenocarbonate 6. The three building blocks 4, 5a, and 6 were prepared stereoselectivly from D-galactose (7), 2,5-anhydro-D-mannitol (8), and L-rhamnose (9), respectively. A new and efficient method for desymmetrization of the C(2)-symmetrical compound 8 is

  通过THP-THF片段2和末端丁烯内酯3的钯催化交叉偶联反应，可实现强大的抗肿瘤产乙酸原素粘液素（1）的总合成。构建片段2的关键过程是螯合-在乙二醛23a中控制乙炔基氯化镁的添加，以及由此制得的烷基锂与THP醛4的缩合。内酯3的合成通过利用无环硒代碳酸酯6的自由基环化而依赖于新方法。这三个结构单元4、5a和6是从D-半乳糖（7），2,5-脱水D立体选择性地制备的-甘露醇（8）和L-鼠李糖（9）。还介绍了一种新的高效的对称对称C（2）化合物8的方法。
• Sugar-based novel chiral macrocycles for inclusion applications and chiral recognition
  作者：Ankita Singh、Vinod Khatri、Shashwat Malhotra、Ashok K. Prasad

  DOI：10.1016/j.carres.2015.12.006

  日期：2016.2

  A convergent template assisted synthesis of sugar-based chiral macrocycles has been achieved. The host-guest inclusion studies have revealed significant interactions of the synthesized macrocycle with primary over secondary ammonium salt. The chiral macrocyle also discriminates between D- and L-phenylalanine methyl ester hydrochlorides as revealed by (1)H NMR spectral studies on the mixture of the

  已经实现了收敛模板辅助的基于糖的手性大环化合物的合成。主客体夹杂物研究表明，合成的大环化合物与伯铵盐相比于伯铵盐具有明显的相互作用。如对主体和客体分子的混合物的（1）1 H NMR光谱研究所揭示的，手性大环化合物还区分了D-和L-苯丙氨酸甲酯盐酸盐。
• Synthesis of Mono- and Bis-C-glycosylated 2,3,4-Trisubstituted 1<i>H</i>-Pyrroles as Cyclo- and Acyclo-<i>C</i>-nucleoside Analogues
  作者：Ernesto Suárez、Carmen Alonso-Cruz、Raimundo Freire、María Rodríguez

  DOI：10.1055/s-2007-991061

  日期：——

  A new method for the synthesis of mono- and bis-C-glycosylated 2,3,4-trisubstituted 1 H-pyrroles, a type of cyclo- and -acyclo- C-nucleoside analogues, is described. The reaction of readily available sensitive 2 H-azirines derived from carbohydrates with 1,3-dicarbonyl compounds is catalysed by tris(triphenylsilyl)vanadate under mild conditions. The reaction of 2 H-azirines with vanadium enolates has

  描述了一种合成单-和双-C-糖基化 2,3,4-三取代 1 H-吡咯（一种环-和-无环-C-核苷类似物）的新方法。在温和条件下，三（三苯基甲硅烷基）钒酸盐可催化由碳水化合物衍生的易获得的敏感 2 H-氮丙啶与 1,3-二羰基化合物的反应。2 H-氮杂与钒烯醇化物的反应以前没有描述过。这种方法可能适用于以三取代的 1 H-吡咯骨架作为分子支架的组合库的合成。
• Antidiabetic phosphates
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0354323A2

  公开（公告）日：1990-02-14

  Phosphates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the en­zyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These phosphates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphates are also disclosed.

  已公开的磷酸盐可刺激果糖-1,6-二磷酸酶，抑制 6-磷酸果糖-1-激酶，从而降低哺乳动物体内的葡萄糖水平。因此，这些磷酸盐可用于治疗高血糖和/或糖尿病。此外，还公开了这些磷酸盐的合成工艺。
• Hydrolytically stable arabinofuranoside analogs for the synthesis of arabinosyltransferase inhibitors
  作者：Manon Chaumontet、Valérie Pons、Karine Marotte、Jacques Prandi

  DOI：10.1016/j.tetlet.2005.12.029

  日期：2006.2

  The first members of two new families of arabinosyltransferase inhibitors, derived from previously reported hybrid compounds covalently associating all iminoalditol with an alpha-D-arabinofuranoside, have been prepared. In place of the arabinofuranoside moiety, they incorporate in their structure a Suitably Substituted tetrahydrofuran (C-glycoside family) or a cyclopentane (carba-sugar family) for mimicking the alpha-D-arabinofuranoside ring. (c) 2005 Elsevier Ltd. All rights reserved.