(5'-formyl-2'-furyl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 851190-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5'-formyl-2'-furyl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 5-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)methyl]-2-furancarboxaldehyde；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(5-formylfuran-2-yl)methoxy]oxan-2-yl]methyl acetate
• CAS: 851190-28-8
• 化学式: C₂₀H₂₄O₁₂
• 分子量: 456.403
• InChiKey: PTEXYVPMPPFVOR-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (5'-formyl-2'-furyl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 Rose Bengal-Sephadex resin 、 氧气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以86%的产率得到(2'-hydroxy-5'-oxo-2',5'-dihydrofuran-2'-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Acetylated Ranunculin Diastereoisomers and δ–Glucosyloxy–γ–Oxo Esters from α or β Glucosylmethylfurfural

  摘要：

  The alpha and beta acetylated (5-formyl-2-furyl)methyl-D-glueopyranosides were synthesized and converted into acetylated ranunculin diastereoisomers and delta-glucosyloxy-gamma-oxo esters.

  DOI：

  10.1081/car-200049688
• 作为产物：
  描述：

  糠醇 在 calcium sulfate 、 碘 、 silver(l) oxide 、 三氯氧磷 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 (5'-formyl-2'-furyl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Acetylated Ranunculin Diastereoisomers and δ–Glucosyloxy–γ–Oxo Esters from α or β Glucosylmethylfurfural

  摘要：

  The alpha and beta acetylated (5-formyl-2-furyl)methyl-D-glueopyranosides were synthesized and converted into acetylated ranunculin diastereoisomers and delta-glucosyloxy-gamma-oxo esters.

  DOI：

  10.1081/car-200049688

文献信息

• Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals
  作者：Dierk Martin、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2005.12.010

  日期：2006.3

  A practical protocol for the elaboration of O-glycosyl-HMF's from glycosyl-(1 -> 6)-glucoses is reported, the two steps involving aluminate-promoted isomerization to the respective 6-O-glycosyl-fructoses and subsequent selective dehydration of the fructose portion. Accordingly, melibiose, gentiobiose, and primeverose are converted into the corresponding 2-uloses and, then, into alpha-GalMF 11, beta-GMF 12, and beta-XylMF 13. Pt/C-catalyzed oxidation with oxygen in NaOH at 25 degrees C efficiently generated the respective furoic acids from alpha-GalMF and alpha-GMF, whilst Pt/O-2 in water at 50 degrees C also oxidizes the primary OH to give the dicarboxylic acids 15 and 17-key building blocks for the generation of novel types of polyesters and polyamides. (c) 2006 Elsevier Ltd. All rights reserved.