(R)-ethyl 2,3-dihydroxy-2-methylpropionate | 69821-00-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (R)-ethyl 2,3-dihydroxy-2-methylpropionate
• 英文别名: ethyl (R)-2,3-dihydroxy-2-methyl-propionate；Ethyl (2R)-2,3-dihydroxy-2-methylpropanoate
• CAS: 69821-00-7
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: CSAJBPPQDTYLCZ-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (R)-ethyl 2,3-dihydroxy-2-methylpropionate 生成 (S)-2,2,4-trimethyl-4-(dimethoxymethyl)-1,3-dioxolane
  参考文献：
  名称：

  Optically active quaternary carbon centers from the photoaddition of chromium-alkoxycarbene complexes and optically active thiazolines

  摘要：

  The photolytic reaction of chromium-alkoxycarbene complexes with valine-derived, optically active thiazolines produced optically active beta-lactam penam derivatives in fair to good yield and with high diastereoselectivity. In most cases alcoholosis of the beta-lactam followed by solvolysis of the thiazolidine ring produced optically active quaternary centers having carbon substituents in four different oxidation states-alkane, alkoxy, aldehyde, and ester. The absolute configuration of the stereogenic center could be inverted by a sequence of redox manipulations of the ester and aldehyde group, making either enantiomer available from the same precursor.

  DOI：

  10.1021/jo00031a025
• 作为产物：
  描述：

  2-甲基-2-(苯基甲氧基)丙二酸1-乙酯 在 palladium on activated charcoal sodium tetrahydroborate 、 氯化亚砜 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-ethyl 2,3-dihydroxy-2-methylpropionate
  参考文献：
  名称：

  总合成vonα-生育酚。4. Mitteilung。三甲基氢chinon和einem optischaktiven C 4 - bzw的Aufbau des Chromanringsystems。C 5- Synthon †

  摘要：

  天然α-生育酚的全合成

  DOI：

  10.1002/hlca.19790620735

文献信息

• Synthesis of (S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol and
  申请人：Hoffmann-La Roche Inc.

  公开号：US04153614A1

  公开（公告）日：1979-05-08

  A process if disclosed for producing (S)-(+)-6-hydroxy-2,4,7,8-tetramethylchroman-2-methanol from either alkyl(R)-2-benzyloxy-3-hydroxy-2-methyl-propionate or (S)-2,2,4-trimethyl-1,3-dioxolan-4-ethanol including intermediates in this synthesis.

  本发明揭示了一种从烷基（R）-2-苄氧基-3-羟基-2-甲基-丙酸酯或（S）-2,2,4-三甲基-1,3-二氧杂环戊醇中制备（S）-（+）-6-羟基-2,4,7,8-四甲基-2-色酚甲醇的过程，包括在合成过程中的中间体。
• Intermediates in the synthesis of vitamin E
  申请人：Hoffmann-La Roche Inc.

  公开号：US04234490A1

  公开（公告）日：1980-11-18

  A process is disclosed for producing (S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol from either alkyl(R)-2-benzyloxy-3-hydroxy-2-methyl-propionate or (S)-2,2,4-trimethyl-1,3-dioxolan-4-ethanol including intermediates in this synthesis.

  本发明公开了一种从烷基（R）-2-苄氧基-3-羟基-2-甲基-丙酸酯或（S）-2,2,4-三甲基-1,3-二氧杂环戊醇中制备（S）-(+)-6-羟基-2,5,7,8-四甲基色基-2-甲醇的过程，包括在此合成中的中间体。
• Hydroquinones
  申请人：Hoffmann-La Roche Inc.

  公开号：US04201879A1

  公开（公告）日：1980-05-06

  A process is disclosed for producing (S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol from either alkyl(R)-2-benzyloxy-3-hydroxy-2-methyl-propionate or (S)-2,2,4-trimethyl-1,3-dioxolan-4-ethanol including intermediates in this synthesis.

  本发明揭示了一种从烷基（R）-2-苄氧基-3-羟基-2-甲基-丙酸酯或（S）-2,2,4-三甲基-1,3-二氧杂环戊醇中制备（S）-(+)-6-羟基-2,5,7,8-四甲基色基-2-甲醇的过程，包括在此合成中的中间体。
• US4234490A
  申请人：——

  公开号：US4234490A

  公开（公告）日：1980-11-18
• Optically active quaternary carbon centers from the photoaddition of chromium-alkoxycarbene complexes and optically active thiazolines
  作者：Douglas K. Thompson、Naoki Suzuki、Louis S. Hegedus、Yoshitaka Satoh

  DOI：10.1021/jo00031a025

  日期：1992.2

  The photolytic reaction of chromium-alkoxycarbene complexes with valine-derived, optically active thiazolines produced optically active beta-lactam penam derivatives in fair to good yield and with high diastereoselectivity. In most cases alcoholosis of the beta-lactam followed by solvolysis of the thiazolidine ring produced optically active quaternary centers having carbon substituents in four different oxidation states-alkane, alkoxy, aldehyde, and ester. The absolute configuration of the stereogenic center could be inverted by a sequence of redox manipulations of the ester and aldehyde group, making either enantiomer available from the same precursor.