(R)-4-[(R)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane | 862670-55-1

• 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: (R)-4-[(R)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 862670-55-1
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: ZFUPITALJCQEJG-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-4-[(R)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 43.92h， 生成 (2R,3R)-2-Benzyloxy-1-[(4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-5-(4-methoxy-benzyloxy)-3-methyl-pentan-1-ol
  参考文献：
  名称：

  Synthesis of the common left-half part of pectenotoxins

  摘要：

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.062
• 作为产物：
  描述：

  (2R,3R)-1,2-O-isopropylidene-5-hexene-1,2,3-triol 、 4-甲氧基氯苄 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以99%的产率得到(R)-4-[(R)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of the common left-half part of pectenotoxins

  摘要：

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.062

文献信息

• Convergent Strategy Towards the Synthesis of Restricted Analogues of Peloruside A
  作者：Nicolas Zimmermann、Pierre Pinard、Bertrand Carboni、Pascal Gosselin、Catherine Gaulon-Nourry、Gilles Dujardin、Sylvain Collet、Jacques Lebreton、Monique Mathé-Allainmat

  DOI：10.1002/ejoc.201201728

  日期：2013.4

  A rapid convergent strategy to access unsaturated analogues of peloruside A has been demonstrated. This is depicted as an original C11-C12 aldol connection between a C12-C20 ketone fragment and a C2-C11 pyran fragment bearing an aldehyde function, with high yield and a good level of diastereoselectivity. The desired unsaturated macrocycle was obtained by a late-stage ring closing metathesis reaction

  已经证明了一种获取 peloruside A 的不饱和类似物的快速收敛策略。这被描述为 C12-C20 酮片段和带有醛官能团的 C2-C11 吡喃片段之间的原始 C11-C12 醛醇连接，具有高产率和良好的非对映选择性。通过后期闭环复分解反应获得所需的不饱和大环。