<(2R,4R)-6-methoxy-4-(4-methoxybenzyl)-oxy-tetrahydropyran-2-yl>-acetic acid methyl ester | 246859-64-3

• 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: <(2R,4R)-6-methoxy-4-(4-methoxybenzyl)-oxy-tetrahydropyran-2-yl>-acetic acid methyl ester
• 英文别名: methyl 2-[(2R,4R)-6-methoxy-4-[(4-methoxyphenyl)methoxy]oxan-2-yl]acetate
• CAS: 246859-64-3
• 化学式: C₁₇H₂₄O₆
• 分子量: 324.374
• InChiKey: FWBFFYWGTFDTLJ-BLBXNVQISA-N

物化性质

• 沸点：
  420.3±45.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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,4R)-6-methoxy-4-(4-methoxybenzyl)-oxy-tetrahydropyran-2-yl>-acetic acid methyl ester 在 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 sodium hydride 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  Versatile 8-Oxabicyclo[3.2.1]oct-6-en-3-one:  Stereoselective Methodology for Generating C-Glycosides, δ-Valerolactones, and Polyacetate Segments

  摘要：

  [GRAPHICS]A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta -valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported, Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.

  DOI：

  10.1021/ol006737a
• 作为产物：
  描述：

  甲醇 、 (1R,3R,5S,6R)-3-(4-methoxybenzyl)-oxy-8-oxa-bicyclo<3.2.1>octan-6-ol 在 pyridinium chlorochromate 、 间氯过氧苯甲酸 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 <(2R,4R)-6-methoxy-4-(4-methoxybenzyl)-oxy-tetrahydropyran-2-yl>-acetic acid methyl ester
  参考文献：
  名称：

  Versatile 8-Oxabicyclo[3.2.1]oct-6-en-3-one:  Stereoselective Methodology for Generating C-Glycosides, δ-Valerolactones, and Polyacetate Segments

  摘要：

  [GRAPHICS]A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta -valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported, Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.

  DOI：

  10.1021/ol006737a

文献信息

• trans-C-Glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one — Synthesis of the C3–C13 segment of the phorboxazoles A and B
  作者：Peter Wolbers、H Martin、R Hoffmann

  DOI：10.1016/s0040-4020(98)01196-x

  日期：1999.2

  The enantiopure and fully resolved C3-C13 segment of the phorboxazoles A and B has been prepared in 14 steps in 24% overall yield starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one. Key steps are the desymmetrization of the oxabicyclic ketone, the anomeric allylation and the asymmetric allylboration. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of enantiopure C-glycosides and pseudo C-glycosides: Lewis-acid mediated heterolysis of methyl acetals
  作者：Oliver Gaertzen、Andrea M. Misske、Peter Wolbers、H.M.R. Hoffmann

  DOI：10.1016/s0040-4039(99)01224-1

  日期：1999.8

  Lewis-acid mediated heterolysis of substituted methoxy acetals derived from anomeric [3.3.1] oxabicyclic lactones leads to enantiopure deoxy C-glycosides in excellent chemical yield. An alternative route to C-glycosidic esters involves simple one-step opening of [3.3.1] oxabicyclic lactones with in situ esterification. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Versatile 8-Oxabicyclo[3.2.1]oct-6-en-3-one:  Stereoselective Methodology for Generating <i>C</i>-Glycosides, δ-Valerolactones, and Polyacetate Segments
  作者：A. Vakalopoulos、H. M. R. Hoffmann

  DOI：10.1021/ol006737a

  日期：2001.1.1

  [GRAPHICS]A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta -valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported, Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.