methyl (2R,3S)-2,3-dihydroxy-3-(4'-methylphenyl)propanoate | 206346-42-1

• 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: methyl (2R,3S)-2,3-dihydroxy-3-(4'-methylphenyl)propanoate
• 英文别名: (2R,3S)-methyl 2,3-dihydroxy-3-(4-methylphenyl)propanoate；methyl (2R,3S)-2,3-dihydroxy-3-(4-methylphenyl)propanoate
• CAS: 206346-42-1
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: KKARZZPCHNOOJZ-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2,3-dihydroxy-3-(4'-methylphenyl)propanoate 在 palladium on activated charcoal 原乙酸三甲酯 、 对甲苯磺酸 、 乙酰溴 、 氢气 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 90.0h， 以0.780 g的产率得到methyl (R)-2-hydroxy-3-(4-methylphenyl)propanoate
  参考文献：
  名称：

  The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α,β-dihydroxy esters

  摘要：

  alpha,beta-Dihydroxy-beta-aryl esters obtained via Sharpless asymmetric dihydroxylation (AD) of substituted cinnamate esters are reduced by sequential reaction with trimethyl orthoacetate and acetyl bromide followed by catalytic hydrogenolysis in methanol to give enantiomerically enriched beta-aryl-alpha-hydroxy esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01176-0
• 作为产物：
  描述：

  4-methylcinnamic acid 在 四氧化锇 、 N-甲基吲哚酮 、 硫酸 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 methyl (2R,3S)-2,3-dihydroxy-3-(4'-methylphenyl)propanoate
  参考文献：
  名称：

  The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α,β-dihydroxy esters

  摘要：

  alpha,beta-Dihydroxy-beta-aryl esters obtained via Sharpless asymmetric dihydroxylation (AD) of substituted cinnamate esters are reduced by sequential reaction with trimethyl orthoacetate and acetyl bromide followed by catalytic hydrogenolysis in methanol to give enantiomerically enriched beta-aryl-alpha-hydroxy esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01176-0

文献信息

• Lipase-catalyzed transesterification as a practical route to homochiral syn-1,2-diols. The synthesis of the taxol side chain
  作者：Donghyun Lee、Mahn-Joo Kim

  DOI：10.1016/s0040-4039(98)00147-6

  日期：1998.4

  syn-2,3-Dihydoxy-3-phenyl-propanoic acid methyl ester (1a) and its simple derivatives (1b-e) are efficiently resolved in LPS-catalyzed transesterification, leading to the synthesis of the taxol side chain and analogs from both resolved enantiomers.

  syn -2,3-二羟基-3-苯基丙酸甲酯（1a）及其简单衍生物（1b-e）在LPS催化的酯交换反应中得到有效拆分，从而导致紫杉醇侧链及其类似物的合成拆分的对映体。
• Improved large-scale synthesis of phenylisoserine and the taxol C-13 side chain
  作者：Michael V Voronkov、Alexander V Gontcharov、Zhi-Min Wang

  DOI：10.1016/s0040-4039(02)02434-6

  日期：2003.1

  Dihydrodihydroxycinnamic acids and their esters react with acetonitrile or benzonitrile in the presence of sulfuric acid to afford the corresponding syn-β-amino-α-hydroxypropionic acid derivatives. High yields and diastereoselectivity of this transformation allows preparation of various phenylisoserine derivatives on a practical scale.

  在硫酸存在下，二氢二羟基肉桂酸及其酯与乙腈或苄腈反应，得到相应的顺-β-氨基-α-羟基丙酸衍生物。该转化的高产率和非对映选择性允许以实际规模制备各种苯基异丝氨酸衍生物。
• A Strategy for the Asymmetric Aminohomologation of α,β-Dihydroxy Aldehydes:  Application to the Synthesis of the Southwest Tripeptide Segment of Echinocandin B
  作者：Claudio Palomo、Mikel Oiarbide、Aitor Landa

  DOI：10.1021/jo990964c

  日期：2000.1.1

  The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic acid methyl ester, a completely diastereoselective [2 + 2] hydroxyketene-imine cycloaddition, and the TEMPO-assisted cyclo-expansion of the resulting 3-hydroxy beta-lactam to the corresponding alpha-amino acid N-carboxy anhydride (NCA). The smooth opening of the latter upon treatment with L-Thr((OSiBuPh2)-Bu-t)OMe and further acylation with the N-Cbz protected L-4-tert-butyldiphenylsilyloxy proline rendered the southwest portion of echinocandin B.
• The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α,β-dihydroxy esters
  作者：Nicholas J Lawrence、Stephen Brown

  DOI：10.1016/s0040-4020(01)01176-0

  日期：2002.1

  alpha,beta-Dihydroxy-beta-aryl esters obtained via Sharpless asymmetric dihydroxylation (AD) of substituted cinnamate esters are reduced by sequential reaction with trimethyl orthoacetate and acetyl bromide followed by catalytic hydrogenolysis in methanol to give enantiomerically enriched beta-aryl-alpha-hydroxy esters. (C) 2002 Elsevier Science Ltd. All rights reserved.