[(2R,3R,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl acetate | 314249-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: [(2R,3R,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl acetate
• CAS: 314249-12-2
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: GMZYXHADNYFVHU-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl acetate 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以62%的产率得到(4R,5R,6R)-4,5-dimethoxy-6-(methoxymethyl)-3-methylideneoxan-2-one
  参考文献：
  名称：

  Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived α-Methylene-δ-valerolactones from C-2-Acetoxymethyl Glycals

  摘要：

  C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H(R), montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)(4) as catalysts. Exclusive alpha or beta selectivities have been observed with various primary, secondary and tertiary alcohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding alpha -methylene-delta -valerolactones in good yields in one step using m-CPBA in the presence of BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00775-4
• 作为产物：
  描述：

  乙酸酐 、 1,5-anhydro-2-deoxy-2-formyl-3,4,6-tri-O-methyl-D-lyxo-hex-1-enitol 在 sodium tetrahydroborate 、 吡啶 作用下， 以 甲醇 为溶剂， 反应 0.42h， 以84%的产率得到[(2R,3R,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived α-Methylene-δ-valerolactones from C-2-Acetoxymethyl Glycals

  摘要：

  C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H(R), montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)(4) as catalysts. Exclusive alpha or beta selectivities have been observed with various primary, secondary and tertiary alcohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding alpha -methylene-delta -valerolactones in good yields in one step using m-CPBA in the presence of BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00775-4

文献信息

• Tailor-made chiral pyranopyrans based on glucose and galactose and studies on self-assembly of some crystals and low molecular weight organogel (LMOG)
  作者：Soumik Roy、Arijit Chakraborty、Basab Chattopadhyay、Abir Bhattacharya、Alok K. Mukherjee、Rina Ghosh

  DOI：10.1016/j.tet.2010.08.054

  日期：2010.10

  InCl3 catalyzed reactions of 2-C-acetoxymethylglycal derivatives with different phenolic compounds resulted in the formation of sugar based pyranoarenopyrans in good yields and moderate to excellent diastereoselectivity in favor of 10aR- or 12aR- or 14aR-products. One of the synthesized compounds, viz. (2R,3R,12aR)-2,3,5,12a-tetrahydro-2-methoxymethyl-3-methoxypyrano[2,3-b]naphtho[1,2-e]pyran gelated polar solvents like MeOH, EtOH and non-polar solvents like pentane, hexane, heptane, octane, pet. ether, etc. The SEM picture of the corresponding hexane xerogel exhibited a rare type of microtubular gel assembly, whereas the SEM pictures of MeOH and pet. ether xerogels showed different types of three-dimensional network. Study of the MeOH gel by Fluorescence spectroscopy, H-1 NMR and X-ray powder diffraction analysis indicated that the supramolecular assembly in the MeOH gel can be attributed to pi-stacking. The crystal packing of (2R.3R,10aR)-3,10a-dihydro-2-methoxymethyl-3-methoxy-7-methyl-2H,5H-pyrano[2,3-b][1]benzopyran, a benzopyran analogue of the above organogelator was stabilized by C-H center dot center dot center dot O and C-H center dot center dot center dot pi hydrogen bonds forming one-dimensional columns parallel to the [001] direction, whereas the corresponding benzopyran 3-epimer showed only C-H center dot center dot center dot O hydrogen bonds among the molecules. (C) 2010 Elsevier Ltd. All rights reserved.
• Crystal or Low Molecular Mass Organogel Based on Sugar-Derived Chiral Pyrano[2,3-<i>b</i>]naphtho[1,2-<i>e</i>]pyrans
  作者：Rina Ghosh、Arijit Chakraborty、Dilip K. Maiti、Vedavati G. Puranik

  DOI：10.1021/ol052963e

  日期：2006.3.1

  2-C-Acetoxymethyl glycal derivatives reacted with beta-naphthol in the presence of InCl3 (30 mol %) to give chiral pyrano[2,3-b]naphtho[1,2-e]-pyrans in good to excellent yields via stereoselective Ferrier rearrangement-tandem cyclization. The major glucose-derived product exhibited crystal packing with C-(HO)-O-... and C-H-...pi (arene) interactions and the major galactose-derived product, a low molecular mass organogelator (LMOG), formed a rare type of micro tubular gel assembly in n-hexane.