[(2S)-6-hydroxy-2-(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-2-yl]methyl acetate | 479353-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [(2S)-6-hydroxy-2-(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-2-yl]methyl acetate
• CAS: 479353-37-2
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: HBGRPKBZYBYBIS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S)-6-hydroxy-2-(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-2-yl]methyl acetate 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 2H-1-苯并吡喃-2-甲醇,3,4-二氢-6-羟基-2,5,7,8-四甲基-,(2R)-
  参考文献：
  名称：

  Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative

  摘要：

  The stereoselective acylation of an achiral chromandimethanol derivative by vinyl acetate in the presence of Candida antarctica lipase in organic media gave the corresponding (S)-monoester in high enantiomeric purity (ee=98%). (S)-alpha-Tocotrienol was synthesized in 19% overall yield over six steps from this (S)-monoester. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01865-8
• 作为产物：
  描述：

  乙酸乙烯酯 、 2,2-Bis(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-6-ol 在 Candida antarctica lipase 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以60%的产率得到[(2S)-6-hydroxy-2-(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative

  摘要：

  The stereoselective acylation of an achiral chromandimethanol derivative by vinyl acetate in the presence of Candida antarctica lipase in organic media gave the corresponding (S)-monoester in high enantiomeric purity (ee=98%). (S)-alpha-Tocotrienol was synthesized in 19% overall yield over six steps from this (S)-monoester. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01865-8

文献信息

• Chemoenzymatic synthesis of both enantiomers of α-tocotrienol
  作者：Robert Chênevert、Gabriel Courchesne、Nicholas Pelchat

  DOI：10.1016/j.bmc.2006.03.035

  日期：2006.8

  The stereoselective acylation of the achiral chromanedimethanol derivative 1 by vinyl acetate in the presence of Candida antarctica lipase B gave the (S)-monoester 2 in high enantiomeric purity (ee >= 98%). Enzymatic hydrolysis of diesters of compound I failed to give (R)-monoester 2 in good yield and high ee. Thus, both enantiomers of alpha-tocotrienol were synthesized from the (S)-monoester 2. (c) 2006 Elsevier Ltd. All rights reserved.