4(R),5(R)-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde | 112709-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4(R),5(R)-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde
• 英文别名: (4R,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde；4-Deoxy-2,3-O-isopropyliden-D-erythrose
• CAS: 112709-74-7
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: BWFCUWGVXQIDQS-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4(R),5(R)-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 1.25h， 生成
  参考文献：
  名称：

  Achmad, Sjamsul; Hoeyer, Thomas; Kjaer, Anders, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 8, p. 599 - 609

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-methanol 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 4(R),5(R)-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde
  参考文献：
  名称：

  Versicolactones A and B: total synthesis and structure revision

  摘要：

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.120

文献信息

• Decarboxylative Mannich Reactions
  作者：Maximillian Böhm、Kerstin Proksch、Rainer Mahrwald

  DOI：10.1002/ejoc.201201644

  日期：2013.2

  p-Methoxyphenylimines obtained from enolizable aldehydes react in the absence of catalysts at room temperature with β-keto carboxylic acids through a decarboxylative Mannich reaction. The Mannich products were obtained with a high degree of anti selectivity. By use of chiral oxygen-containing aldehydes, operationally simple access to aminohydroxylated polyketide substructures is possible.

  由可烯醇化醛获得的对甲氧基苯基亚胺在没有催化剂的情况下在室温下通过脱羧曼尼希反应与 β-酮羧酸反应。以高度的抗选择性获得曼尼希产物。通过使用手性含氧醛，可以在操作上简单地获得氨基羟基化聚酮化合物亚结构。
• Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde
  作者：W. H. Binder、R. H. Prenner、W. Schmid

  DOI：10.1007/bf01277638

  日期：1994.6

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.
• FRONZA, GIOVANNI;FUGANTI, CLAUDIO;PEDROCCHI-FANTONI, GIUSEPPE;PIZZI, DOME+, J.CARBOHYDR. CHEM., 7,(1988) N 1, 33-47
  作者：FRONZA, GIOVANNI、FUGANTI, CLAUDIO、PEDROCCHI-FANTONI, GIUSEPPE、PIZZI, DOME+

  DOI：——

  日期：——
• TAMURA, YASUMITSU;TAMURA, OSAMU;ITO, FUMIO;KITA, YASUXIKO
  作者：TAMURA, YASUMITSU、TAMURA, OSAMU、ITO, FUMIO、KITA, YASUXIKO

  DOI：——

  日期：——
• Versicolactones A and B: total synthesis and structure revision
  作者：Liping Wang、Weiming Zhu

  DOI：10.1016/j.tetlet.2013.09.120

  日期：2013.12

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.