allyl-4,6-O-benzylidene-2,3-di-O-hydroxy-D-mannopyranoside | 1056479-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl-4,6-O-benzylidene-2,3-di-O-hydroxy-D-mannopyranoside
• 英文别名: allyl 4,6-di-O-benzylidene-D-mannopyranoside；allyl 4,6-O-benzylidene-D-mannopyranoside
• CAS: 1056479-53-8
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: OMBCPFYQIULSGV-VAZACWIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl-4,6-O-benzylidene-2,3-di-O-hydroxy-D-mannopyranoside 在 {Ir(COD)[PCH₃(C₆H₅)2]}PF₆ 水 、 sodium hydride 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,3-di-O-benzyl-4,6-O-benzylidene-D-mannopyranose
  参考文献：
  名称：

  Stereochemical control in hex-5-enyl radical cyclizations: from carbohydrates to carbocycles. 3

  摘要：

  DOI：

  10.1021/ja00187a031
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 AGMP resin 、 四氯化锡 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 1.5h， 生成 allyl-4,6-O-benzylidene-2,3-di-O-hydroxy-D-mannopyranoside
  参考文献：
  名称：

  Stereochemical control in hex-5-enyl radical cyclizations: from carbohydrates to carbocycles. 3

  摘要：

  DOI：

  10.1021/ja00187a031

文献信息

• Synthetic 3-<i>O</i>-Methylmannose-Containing Polysaccharides (<i>s</i>MMPs):  Design and Synthesis
  作者：Margaret C. Hsu、Jinhwa Lee、Yoshito Kishi

  DOI：10.1021/jo061991n

  日期：2007.3.1

  With the hope of mimicking the chemical and biological properties of natural 3-O-methylmannose-containing polysaccharides (MMPs), synthetic 3-O-methylmannose-containing polysaccharides (sMMPs) were designed and synthesized in a convergent manner. With little modification of the Mukaiyama glycosidation, high α-selectivity (>50:1∼>20:1) and yields (79∼74%) were achieved for the key glycosidation steps

  希望模仿天然的含3 - O-甲基甘露糖的多糖（MMP）的化学和生物学特性，合成的含3 - O-甲基甘露糖的多糖（sMMPs以收敛的方式设计和合成。几乎没有对Mukaiyama糖苷化反应进行修饰的情况，关键糖苷化步骤的α-选择性高（> 50：1至> 20：1），收率（79％至74％）。已显示观察到的异常高的α-选择性是由于在糖苷化条件下β-向α-异构体的选择性异构化。这种糖苷化非常适合于高度收敛的寡糖合成，特别是因为即使以大约1：1的摩尔比使用大小相等的供体和受体时，化学产率也很高。迭代反应顺序允许生长低聚糖每个循环后尺寸加倍，并导致的有效合成小号MMP 8-，12-，和16聚体18 - 20。
• Ceric ammonium nitrate/acetic anhydride: A tunable system for the <i>O</i>-acetylation and mononitration of diversely protected carbohydrates
  作者：Mohindra Seepersaud、Savita Seecharan、Lorale J. Lalgee、Nigel Kevin Jalsa

  DOI：10.1080/00397911.2016.1230219

  日期：2017.5.3

  ABSTRACT Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the esterified products being furnished in good yields. Apart from affording the O-acetylated products, their mononitrated counterparts were also

  摘要 使用乙酸酐和催化量的硝酸铈铵 (CAN) 实现了多种部分保护的碳水化合物衍生物的酯化。证明了与常用保护基团的相容性，酯化产物以良好的产率提供。除了提供 O-乙酰化产物外，还产生了它们的单硝化对应物，这取决于起始材料的反应性。降低 CAN 的摩尔当量只能提供 O-乙酰化产物，而增加它有利于单硝化衍生物。图形概要
• Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers
  作者：Firoz A. Jaipuri、Nicola L. Pohl

  DOI：10.1039/b803451f

  日期：——

  We report herein the first synthesis of linear and branched mannose oligosaccharides using fluorous-tag assistance with reagents and FSPE protocols that are amenable to automation. The particular fluorous linker proved to maintain solubility of the growing oligosaccharide chain such that identical reaction solvent conditions and purification protocols could be used between glycosylation and deprotection reactions, thereby rendering the procedures amenable to automation.

  我们在本文中首次报道了利用荧光标记辅助试剂和可实现自动化的 FSPE 方案合成线性和支链甘露寡糖的过程。事实证明，这种特殊的荧光连接剂能保持不断增长的寡糖链的溶解性，因此在糖基化反应和脱保护反应之间可以使用相同的反应溶剂条件和纯化方案，从而使程序适合自动化。
• Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
  作者：Rie Namme、Takashi Mitsugi、Hideyo Takahashi、Moto Shiro、Shiro Ikegami

  DOI：10.1016/j.tet.2006.07.032

  日期：2006.9

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.