(2R,6R)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran | 790667-24-2

• 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,6R)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran
• 英文别名: (2R,6R)-6-methoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran
• CAS: 790667-24-2
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: DGIDIHDKOKZGLX-ZIAGYGMSSA-N

物化性质

• 沸点：
  341.6±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,6R)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.5h， 生成 (1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane
  参考文献：
  名称：

  Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

  摘要：

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.

  DOI：

  10.1021/jo0493774
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 吡啶 、 titanium(IV) isopropylate 、 三氟甲磺酸三甲基硅酯 、 TEA 、 镍 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.08h， 生成 (2R,6R)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

  摘要：

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.

  DOI：

  10.1021/jo0493774

文献信息

• The high-pressure [4+2]cycloaddition of 1-methoxybuta-1,3-diene to the glycolaldehyde-derived heterodienophiles, catalyzed by chiral metallosalen complexes
  作者：Piotr Kwiatkowski、Wojciech Chaładaj、Małgorzata Malinowska、Monika Asztemborska、Janusz Jurczak

  DOI：10.1016/j.tetasy.2005.07.031

  日期：2005.9

  A high-pressure (ca. 10 kbar) reaction of 1-methoxybuta-1,3-diene 1 with variously O-protected glycolaldehydes 2, catalyzed by the chiral (salen)Cr(III)Cl 4a–d and 5 or (salen)Co(II) 6a–f and 7 complexes, has been studied. The best results were obtained for tert-butyldimethylsilyloxyacetaldehyde 2a. The reaction afforded, in good yield (up to 90%) and with very good diastereoselectivity (up to 92%)

  手性（salen）Cr（III）Cl 4a – d和5或（salen ）催化的1-甲氧基丁1,3-二烯1与各种O保护的乙醇醛2的高压（大约10 kbar）反应）Co（II）6a – f和7种配合物已被研究。叔丁基二甲基甲硅烷基氧基乙醛2a获得了最佳结果。该反应以[4 + 2]环加合物3a的高收率（最高90％）和非对映选择性（最高92％）和对映选择性（最高93％ee）提供。，是具有重大合成意义的化合物。讨论了环加成反应的立体化学模型。
• Lewis acid catalyzed cyclocondensations of functionalized dienes with aldehydes
  作者：Samuel Danishefsky、James F. Kerwin、Susumu Kobayashi

  DOI：10.1021/ja00365a095

  日期：1982.1
• Banaszek, Anna, Bulletin of the Polish Academy of Sciences: Chemistry, 1988, vol. 36, # 5-6, p. 277 - 283
  作者：Banaszek, Anna

  DOI：——

  日期：——
• Synthesis of 4-Deoxy-<scp>l</scp>-(and <scp>d</scp>-)hexoses from Chiral Noncarbohydrate Building Blocks
  作者：Romualdo Caputo、Mauro De Nisco、Pasquale Festa、Annalisa Guaragna、Giovanni Palumbo、Silvana Pedatella

  DOI：10.1021/jo0493774

  日期：2004.10.1

  4-Deoxy-L-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-L-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their D-series enantiomers.