2-(4S,6R)-[6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl]ethanol

• 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: 2-(4S,6R)-[6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl]ethanol
• 英文别名: 2-[(4S,6R)-2,2-dimethyl-6-(2-phenylmethoxyethyl)-1,3-dioxan-4-yl]ethanol
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: MRGFUDWELACNBW-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4S,6R)-[6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl]ethanol 在 palladium on activated charcoal 氢气 作用下， 以85%的产率得到2,2'-((4R,6S)-2,2-dimethyl-1,3-dioxane-4,6-diyl)bis(ethan-1-ol)
  参考文献：
  名称：

  Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diols

  摘要：

  A new seven-carbon polyhydroxylated chiral synthon is obtained, as single enantiomer, in nearly quantitative yield by enzymatic desymmetrization of the appropriate meso compound. Pseudomonas fluorescens shows an high degree of enantiotopic discrimination in a particularly complex molecule possessing a 1,3 syn diol structure; likewise, this chiral synthon has been easily transformed into a known compactin analogue.

  DOI：

  10.1021/jo00056a002
• 作为产物：
  描述：

  3-苄氧基-1-丙醇 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 三乙基硼 、 sodium hydride 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(4S,6R)-[6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl]ethanol
  参考文献：
  名称：

  Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diols

  摘要：

  A new seven-carbon polyhydroxylated chiral synthon is obtained, as single enantiomer, in nearly quantitative yield by enzymatic desymmetrization of the appropriate meso compound. Pseudomonas fluorescens shows an high degree of enantiotopic discrimination in a particularly complex molecule possessing a 1,3 syn diol structure; likewise, this chiral synthon has been easily transformed into a known compactin analogue.

  DOI：

  10.1021/jo00056a002

文献信息

• Elongation of 1,3-Polyols via Iterative Catalyst-Directed Carbonyl Allylation from the Alcohol Oxidation Level
  作者：Abbas Hassan、Yu Lu、Michael J. Krische

  DOI：10.1021/ol901136w

  日期：2009.7.16

  Iterative enantioselective carbonyl allylation from the alcohol oxidation level under the conditions of iridium catalyzed transfer hydrogenation enables chain elongation of 1,3-polyols. High levels of catalyst-directed enantioselectivity and diastereoselectivity are observed.

  在铱催化的转移氢化条件下，从醇氧化水平迭代对映选择性羰基烯丙基化使 1,3-多元醇的链延长。观察到高水平的催化剂导向的对映选择性和非对映选择性。
• Preparation of chiral 1,3 skipped anti- and syn-tetrols via highly enantioselective biocatalytic resolution
  作者：Carlo Bonini、Lucia Chiummiento、Maria Funicello

  DOI：10.1016/s0957-4166(01)00467-0

  日期：2001.10

  Biocatalytic resolution of the 7-benzyloxy-3,5-anti-dioxolan-1,3 5,7-tetrol and the 7-benzyloxy-3,5-syn-dioxolan-1,3,5,7-tetrol was found to be highly enantioselective leading to differently functionalized chiral tetrols with significantly high e.e. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diols
  作者：Carlo Bonini、Rocco Racioppi、Giuliana Righi、Licia Viggiani

  DOI：10.1021/jo00056a002

  日期：1993.2

  A new seven-carbon polyhydroxylated chiral synthon is obtained, as single enantiomer, in nearly quantitative yield by enzymatic desymmetrization of the appropriate meso compound. Pseudomonas fluorescens shows an high degree of enantiotopic discrimination in a particularly complex molecule possessing a 1,3 syn diol structure; likewise, this chiral synthon has been easily transformed into a known compactin analogue.
• Enzyme-catalyzed desymmetrization of meso-skipped polyols to useful chiral building blocks
  作者：Carlo Bonini、Rocco Racioppi、Licia Viggiani、Giuliana Righi、Leucio Rossi

  DOI：10.1016/s0957-4166(00)80117-2

  日期：1993.5

  The biocatalytic desymmetrization, in presence of different enzymes, of two models of polyfunctionalized diols in a meso form was studied PFL was found to be the most selective enzyme with excellent results in chemical and optical yield with some of the tested substrates. The obtained chiral building block was utilized for some useful synthetic transformations toward the synthesis of natural products.