(R)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol-p-toluenesulfonate | 79397-61-8

• 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)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol-p-toluenesulfonate
• 英文别名: (R)-6-benzyloxy-2,5,7,8-tetramethyl-2-[2-tosyloxyethyl]chroman；(r)-6-Benzyloxy-2,5,7,8-tetramethyl-2-[2-tosyloxy-ethyl]chroman；2-[(2R)-2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl]ethyl 4-methylbenzenesulfonate
• CAS: 79397-61-8
• 化学式: C₂₉H₃₄O₅S
• 分子量: 494.652
• InChiKey: QHZOCKCDZNOVPR-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol-p-toluenesulfonate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 4.0~22.0 ℃ 、99.99 kPa 条件下， 反应 77.0h， 生成 (2R)-(+)-3,4-dihydro-6-hydroxy-N,N,N,-2,5,7,8-heptamethyl-2H-1-benzopyran-2-ethanaminium 4-methylbenzenesulfonate
  参考文献：
  名称：

  摘要：

  In the presence of lipase from the yeast Candida cylindracea, partial acetylation of (+/-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol with vinyl acetate gives S-(+)-acetate whose alkaline hydrolysis affords (S)-(-)-alcohol. Repeated enzymatic acetylation of the "residual" alcohol up to similar to39% conversion afforded the R-enantiomer. The enantiomeric alcohols were oxidized to (S)- or (R)-aldehydes having the same sign of \alpha\(D) as the original alcohols. These alcohols were converted into S-(+)- and R-(-)-enantiomers of the antioxidant MDL-73404, a hydrophilic analog of alpha-tocopherol.

  DOI：

  10.1023/a:1015001401902
• 作为产物：
  描述：

  (R)-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]acetaldehyde 在 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 49.5h， 生成 (R)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol-p-toluenesulfonate
  参考文献：
  名称：

  摘要：

  In the presence of lipase from the yeast Candida cylindracea, partial acetylation of (+/-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol with vinyl acetate gives S-(+)-acetate whose alkaline hydrolysis affords (S)-(-)-alcohol. Repeated enzymatic acetylation of the "residual" alcohol up to similar to39% conversion afforded the R-enantiomer. The enantiomeric alcohols were oxidized to (S)- or (R)-aldehydes having the same sign of \alpha\(D) as the original alcohols. These alcohols were converted into S-(+)- and R-(-)-enantiomers of the antioxidant MDL-73404, a hydrophilic analog of alpha-tocopherol.

  DOI：

  10.1023/a:1015001401902

文献信息

• Total Synthesis of All Eight Stereoisomers of ?-Tocopheryl Acetate. Determination of their diastereoisomeric and enantiomeric purity by gas chromatography
  作者：Noal Cohen、Clifford G. Scott、Christian Neukom、Rocco J. Lopresti、Giuseppe Weber、Gabriel Saucy

  DOI：10.1002/hlca.19810640422

  日期：1981.6.10

  All eight stereoisomers of α-tocopheryl acetate have been synthesized in a state of high chemical and stereoisomeric purity. Key chiral side-chain intermediates were prepared from (+)-(S)-3-hydroxy-2-methylpropanoic acid. New routes to (2R, 4′ RS, 8′ RS)-α-tocopheryl acetate, a mixture of four diastereoisomers, were also developed. A sensitive gas chromatographic method was developed to determine the

  乙酸α-生育酚酯的所有八种立体异构体均以高化学和立体异构体纯度的状态合成。由（+）-（S）-3-羟基-2-甲基丙酸制备关键的手性侧链中间体。到新的路线（2 - [R，4' RS，8' RS）-α生育酚乙酸酯，四个非对映异构的混合物，也被开发的。开发了一种灵敏的气相色谱方法来测定α-生育酚样品作为甲基醚的非对映异构和对映异构纯度。首次确定天然存在的α-生育酚本质上是单一对映体（2 R，4'R，8'R），合成的全外消旋-α-生育酚是四个外消旋物的等摩尔混合物，而天然（E）-（7 R，11 R）-植物醇是非对映异构体和对映异构体均质的。
• ——
  作者：V. N. Odinokov、A. Yu. Spivak、G. A. Emel"yanova、G. D. Gamalevich、E. P. Serebryakov

  DOI：10.1023/a:1015001401902

  日期：——

  In the presence of lipase from the yeast Candida cylindracea, partial acetylation of (+/-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol with vinyl acetate gives S-(+)-acetate whose alkaline hydrolysis affords (S)-(-)-alcohol. Repeated enzymatic acetylation of the "residual" alcohol up to similar to39% conversion afforded the R-enantiomer. The enantiomeric alcohols were oxidized to (S)- or (R)-aldehydes having the same sign of \alpha\(D) as the original alcohols. These alcohols were converted into S-(+)- and R-(-)-enantiomers of the antioxidant MDL-73404, a hydrophilic analog of alpha-tocopherol.