(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-vinyl-3,4-dihydro-2H-pyran | 296268-52-5

• 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,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-vinyl-3,4-dihydro-2H-pyran
• 英文别名: (2R,3R,4R)-5-ethenyl-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran
• CAS: 296268-52-5
• 化学式: C₂₉H₃₀O₄
• 分子量: 442.555
• InChiKey: LORUAMJFJJOEAA-NLDZOOGBSA-N

物化性质

• 沸点：
  571.5±50.0 °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)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-vinyl-3,4-dihydro-2H-pyran 在 盐酸 、 锌 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  通过Diels-Alder反应合成构象受限的C-糖基α-和β-氨基酸以及糖-氨基氨基糖杂化物。

  摘要：

  [结构：见正文]糖衍生的二烯与α-硝基丙烯酸甲酯和β-硝基丙烯酸乙酯进行Diels-Alder反应，形成相应的环加合物，该环加合物已转化为构象受限的C-糖基α-和β-氨基酸。此外，这些β-氨基酸被转化成糖-氨基脲糖杂合分子。

  DOI：

  10.1021/ol052190u
• 作为产物：
  描述：

  甲基三苯基溴化膦 、 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.33h， 以71%的产率得到(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-vinyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  Glycosidation of 3,4,6-Tri-O-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-C-(β-Methyl)Methylene Glycosides

  摘要：

  Monosaccharidic and disaccharidic 2-C-(beta-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl, and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(beta-methyl)methylene group paves the way for further chemical transformations.

  DOI：

  10.1080/07328300008544109

文献信息

• Stereoselective synthesis of 1,2-annulated-C-Aryl glycosides from carbohydrate-derived terminally unsubstituted dienes and arynes: Application towards synthesis of sugar-fused- or branched- naphthalenes, and C-Aryl glycosides
  作者：Sateesh Dubbu、Ashish Kumar Verma、Kadigachalam Parasuraman、Yashwant D. Vankar

  DOI：10.1016/j.carres.2018.06.001

  日期：2018.7

  Synthesis of 1,2-annulated-C-aryl glycosides has been achieved in a stereoselective manner through the Diels-Alder reaction between carbohydrate-derived terminally unsubstituted dienes and in situ generated arynes. In these reactions, formation of sugar-fused (or branched) naphthalenes was also observed and found to be temperature dependent and thus constituting one of the salient features of this

  通过碳水化合物衍生的末端未取代的二烯与原位生成的芳烃之间的Diels-Alder反应，以立体选择的方式实现了1，2-环化的C-芳基糖苷的合成。在这些反应中，还观察到糖融合的（或支链的）萘的形成，并且发现其与温度有关，因此构成了这项工作的重要特征之一。通过官能化未取代的外双键，可以将1，2-环化的C-芳基糖苷合成为重要的物质，从​​而探索了其重要性。此外，1,2-环化的C-芳基糖苷可通过四个步骤快速进入C-芳基糖苷。
• Parasuraman, Kadigachalam; Dubbu, Sateesh; Chennaiah, Ande, Journal of the Indian Chemical Society, 2020, vol. 97, # 2, p. 187 - 196
  作者：Parasuraman, Kadigachalam、Dubbu, Sateesh、Chennaiah, Ande、Ibrahim Sheriff、Vankar, Yashwant D.

  DOI：——

  日期：——
• Glycosidation of 3,4,6-Tri-<i>O</i>-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-<i>C</i>-(β-Methyl)Methylene Glycosides
  作者：Ben-Ami Feit、Idil Kasuto Kelson、Anke Gerull、Sarah Abramson、Richard R. Schmidt

  DOI：10.1080/07328300008544109

  日期：2000.1

  Monosaccharidic and disaccharidic 2-C-(beta-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl, and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(beta-methyl)methylene group paves the way for further chemical transformations.
• Synthesis of Conformationally Constrained <i>C</i>-Glycosyl α- and β-Amino Acids and Sugar−Carbamino Sugar Hybrids via Diels−Alder Reaction
  作者：K. Jayakanthan、Yashwant D. Vankar

  DOI：10.1021/ol052190u

  日期：2005.11.1

  [structure: see text] Sugar-derived dienes undergo Diels-Alder reactions with methyl alpha-nitro acrylate and ethyl beta-nitro acrylate to form the corresponding cycloadducts which have been converted into conformationally constrained C-glycosyl alpha- and beta-amino acids. Further, these beta-amino acids are converted into sugar-carbamino sugar hybrid molecules.

  [结构：见正文]糖衍生的二烯与α-硝基丙烯酸甲酯和β-硝基丙烯酸乙酯进行Diels-Alder反应，形成相应的环加合物，该环加合物已转化为构象受限的C-糖基α-和β-氨基酸。此外，这些β-氨基酸被转化成糖-氨基脲糖杂合分子。