(2S,4R)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane | 186378-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,4R)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane
• CAS: 186378-98-3
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: IDYWJSQHGBGJTL-SKDRFNHKSA-N

物化性质

• 沸点：
  309.4±37.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2S,4R)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane 在 ethandithiol 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-(-)-1,3-丁二醇
  参考文献：
  名称：

  Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments

  摘要：

  Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-ba which formed respectively, in these conditions have been convened efficiently into the title fragments of spiramycin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01523-2
• 作为产物：
  描述：

  (2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane 在 sodium hydroxide 、 苄基三乙基氯化铵 、 镍 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 (2S,4R)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane
  参考文献：
  名称：

  Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments

  摘要：

  Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-ba which formed respectively, in these conditions have been convened efficiently into the title fragments of spiramycin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01523-2

文献信息

• Asymmetric Synthesis of Functionalized Secondary Alcohols by Catalytic Ring-Cleavage Reactions of Cyclic Acetals Derived from (<i>R</i>)-1,3-Butanediol
  作者：Motoharu Kinugasa、Toshiro Harada、Takayuki Egusa、Katsuhiro Fujita、Akira Oku

  DOI：10.1246/bcsj.69.3639

  日期：1996.12

  t-BuS, EtS, EtO, Ph) (1.1-1.5 molar amount), chiral cyclic acetals 6 derived from (R)-1,3-butanediol and aldehydes undergo an efficient ring-cleavage reaction with the inversion of the stereochemistry at the acetal carbon to give the anti isomer of the corresponding products with high stereoselectivity. The reaction is applicable to acetals derived from aromatic, aliphatic, and α,β-unsaturated aldehydes

  在催化量（0.1-0.2摩尔量）的2-苯基-1,3,2-oxazaborolidin-5-one存在下，由二氯苯基硼烷和N-(三氟甲基磺酰基)-L-苯丙氨酸反应制备，和烯醇甲硅烷基醚 ((R2)2C=C(R3)OTMS；R3 = t-BuS、EtS、EtO、Ph)（1.1-1.5 摩尔量），衍生自 (R)-1,3-丁二醇的手性环状缩醛 6醛类经过有效的开环反应，在缩醛碳上发生立体化学的反转，得到具有高立体选择性的相应产物的反异构体。该反应适用于芳香族、脂肪族和α,β-不饱和醛衍生的缩醛。不仅烯醇甲硅烷基醚，而且甲代烯丙基三甲基硅烷和烯丙基三丁基锡都可以用作亲核试剂，导致相应烯丙基化环裂解产物的反异构体的选择性形成。通过两步序列 ((i) PCC (ii) Bn2NH2(CF3CO2)) 从这些开环产物中去除手性助剂，得到对映体...
• Scalable Total Synthesis of Leucascandrolide A Macrolactone Using a Chiral Phosphoric Acid/CuX Combined Catalytic System
  作者：Shigenobu Umemiya、Naoya Shinagawa、Masahiro Terada

  DOI：10.1021/acs.orglett.3c00450

  日期：2023.3.24

  2% yield. The key steps in this synthesis are the enantioselective allylation reaction by chiral phosphoric acid (CPA)/CuBr cooperative catalysis and the diastereoselective catalytic crotylation in the presence of CPA with CuCl. These catalytic reactions can be performed on a gram scale to afford the desired products with excellent stereoselectivities.

  一种可扩展的 leucascandrolide A 大环内酯的全合成已通过 17 个步骤的最长线性序列从现成的原料中以 31.2% 的产率完成。该合成的关键步骤是手性磷酸 (CPA)/CuBr 协同催化的对映选择性烯丙基化反应和 CPA 与 CuCl 存在下的非对映选择性催化巴豆基化反应。这些催化反应可以在克规模上进行，以提供具有优异立体选择性的所需产物。
• Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments
  作者：P. Breuilles、G. Oddon、D. Uguen

  DOI：10.1016/s0040-4039(97)01523-2

  日期：1997.9

  Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-ba which formed respectively, in these conditions have been convened efficiently into the title fragments of spiramycin. (C) 1997 Elsevier Science Ltd.