(4R)-2-(4-methoxyphenyl)-1,3-dioxane-4-carbaldehyde | 501084-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R)-2-(4-methoxyphenyl)-1,3-dioxane-4-carbaldehyde
• 英文别名: (2R,4R)-2-(4-methoxyphenyl)-1,3-dioxane-4-carbaldehyde
• CAS: 501084-34-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: IWBPCKFTGMXZRD-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (4R)-2-(4-methoxyphenyl)-1,3-dioxane-4-carbaldehyde 在 正丁基锂 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 6.0h， 生成 (1S,3R)-1-[(2R,4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-3-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]propane-1,3-diol
  参考文献：
  名称：

  Synthesis and Conformational Analysis of meso-Ter(1,3-dioxan-4-yls)

  摘要：

  A convergent synthesis of the meso-ter(1,3-dioxanyls) 8-11 has been achieved, starting from two enantiomeric building blocks in each case. The stereogenic centres in the central linkage region were set up by stereocontrolled aldol additions. Structure assignment of the final products was based on comparisons between experimental and calculated (3)J(H,H) coupling constants, which reflect distinct conformer populations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3455::aid-ejoc3455>3.0.co;2-v
• 作为产物：
  描述：

  (+/-)-cis-4-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxane 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以70%的产率得到(4R)-2-(4-methoxyphenyl)-1,3-dioxane-4-carbaldehyde
  参考文献：
  名称：

  Synthesis and Conformational Analysis of meso-Ter(1,3-dioxan-4-yls)

  摘要：

  A convergent synthesis of the meso-ter(1,3-dioxanyls) 8-11 has been achieved, starting from two enantiomeric building blocks in each case. The stereogenic centres in the central linkage region were set up by stereocontrolled aldol additions. Structure assignment of the final products was based on comparisons between experimental and calculated (3)J(H,H) coupling constants, which reflect distinct conformer populations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3455::aid-ejoc3455>3.0.co;2-v

文献信息

• Total Synthesis of the Bicyclic Depsipeptide HDAC Inhibitors Spiruchostatins A and B, 5′′-<i>epi</i>-Spiruchostatin B, FK228 (FR901228) and Preliminary Evaluation of Their Biological Activity
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  DOI：10.1002/chem.200901552

  日期：2009.10.26

  Julia–Kocienski olefination of a 1,3‐propanediol‐derived sulfone and a L‐ or D‐malic acid‐derived aldehyde to access the most synthetically challenging unit, (3S or 3R,4E)‐3‐hydroxy‐7‐mercaptohept‐4‐enoic acid, present in a D‐alanine‐ or D‐valine‐containing segment; ii) a condensation of a D‐valine‐D‐cysteine‐ or D‐allo‐isoleucine‐D‐cysteine‐containing segment with a D‐alanine‐ or D‐valine‐containing

  双环去肽肽组蛋白去乙酰化酶（HDAC）抑制剂spiruchostatins A和B，5'′- epi- spiruchostatin B和FK228可以通过聚合和统一的方式高效合成。合成方法涉及以下关键步骤：i）1，3-丙二醇衍生的砜和L-或D-苹果酸衍生的醛的Julia-Kocienski烯化反应，以合成最具挑战性的单元（3 S或3 R，4 E）-3-羟基-7-巯基庚基-4-烯酸，存在于含有D-丙氨酸或D-缬氨酸的链段中；ii）D-缬氨酸-D-半胱氨酸-或D的缩合-同种异体-isoleucine- d -半胱氨酸含与段d -alanine-或d含缬氨酸段直接组装相应的开环-acids; 和iii）的大环化开环使用椎名法或光延法构造必需15-或16-元大环内酯-酸。本合成已建立了螺旋藻抑素B的C5'立体化学。此外，对合成的二肽的HDAC抑制测定和细胞生长抑制分析确定了其效力的顺序，并揭示了
• Highly diastereoselective aldol additions to five-ring N,O-acetals
  作者：Martin Brunner、Ari M.P Koskinen

  DOI：10.1016/j.tetlet.2004.02.104

  日期：2004.4

  Highly diastereoselective aldol additions of pure (2R,4S)-2-tert-butyloxazolidinone-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 1 are reported. While achiral carbonyl compounds lead to mixtures of diastereomers, the double stereodifferentiation of chiral aldehydes gave a single product isomer. The relative and absolute configurations of the aldol products were assigned by NOESY.

  的纯高度非对映醛醇添加剂（2 - [R，4小号）-2-叔-butyloxazolidinone -3,4-二甲酸3-叔丁酯4-甲酯1中报告。尽管非手性羰基化合物可生成非对映异构体的混合物，但手性醛的双立体分化可得到单一产物异构体。羟醛产物的相对和绝对构型由NOESY确定。
• Diastereoselective formation of highly functionalised α-substituted amino acid derivatives via aldol addition
  作者：Martin Brunner、Maija Nissinen、Kari Rissanen、Thomas Straub、Ari M.P. Koskinen

  DOI：10.1016/j.molstruc.2004.09.020

  日期：2005.1

  Highly diastereoselective aldol additions of (2R,4S)-3-tert-butyl 4-methyl 2-tert-butyloxazolidine-3,4-dicarboxylate (1) are reported. The utility of the highly substituted oxazolidines of type 1 for diastereoselective alpha-addition of the fully protected amino acid L-serine with achiral and chiral carbonyl compounds is demonstrated and the relative and absolute configuration of the aldol products are discussed on the basis of NOESY data and solid state structures of selected examples. The aldol products represent highly useful intermediates in the syntheses of sphingosine-related metabolites. (C) 2004 Elsevier B.V. All rights reserved.