[(2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate | 525548-20-3

• 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,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 525548-20-3
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: LDRPNISUWKHEMQ-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 以86%的产率得到methyl 6-O-acetyl-4-deoxy-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  A Versatile Route to l-Hexoses:  Synthesis of l-Mannose and l-Altrose

  摘要：

  [GRAPHICS]An efficient route for the synthesis of orthogonally protected L-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-L-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-L-pyranoside, which can be suitably functionalized to afford the desired L-hexoses. In this paper, we report the synthesis of L-manno- and L-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

  DOI：

  10.1021/ol061916z
• 作为产物：
  描述：

  3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-[1,4]dithiine-2-carbaldehyde 在 Amberlyst 15 、 镍 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 [(2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
  参考文献：
  名称：

  A Versatile Route to l-Hexoses:  Synthesis of l-Mannose and l-Altrose

  摘要：

  [GRAPHICS]An efficient route for the synthesis of orthogonally protected L-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-L-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-L-pyranoside, which can be suitably functionalized to afford the desired L-hexoses. In this paper, we report the synthesis of L-manno- and L-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

  DOI：

  10.1021/ol061916z

文献信息

• The High-Pressure [4+2] Cycloaddition of Activated 1,3-Dienes to Nonactivated­ Heterodienophiles Derived from Glycolaldehyde
  作者：Janusz Jurczak、Małgorzata Malinowska、Piotr Sałań、Jean-Claude Caille

  DOI：10.1055/s-2002-35985

  日期：——

  [4+2] Cycloaddition of 1,3-dienes to glycolaldehyde derivatives, leading to 5,6-dihydro-2H-pyrans, was effected by high pressure (10 kbar) in the presence of Eu(fod)3 (2%). Enantioselective version of the reaction was also studied.

  在 Eu(fod)3 (2%) 存在下，通过高压（10 千巴）将 1,3 二烯与乙醛衍生物进行 [4+2] 环加成反应，生成 5,6 二氢-2H-吡喃。 还研究了该反应的对映体选择性。
• 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。
• 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：——
• Berube, Gervais; Luce, Eric; Jankowski, Krzysztof, Bulletin de la Societe Chimique de France, 1983, vol. 2, # 3-4, p. 109 - 111
  作者：Berube, Gervais、Luce, Eric、Jankowski, Krzysztof

  DOI：——

  日期：——