(4R,4'S,5R,5'S)-2,2,2',2'-tetramethyl-5'-vinyl-[4,4'-bi(1,3-dioxolan)]-5-ol | 289493-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,4'S,5R,5'S)-2,2,2',2'-tetramethyl-5'-vinyl-[4,4'-bi(1,3-dioxolan)]-5-ol
• CAS: 289493-31-8
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: CGSJQFXMHVUDSC-AXTSPUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,4'S,5R,5'S)-2,2,2',2'-tetramethyl-5'-vinyl-[4,4'-bi(1,3-dioxolan)]-5-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 (3aS,5aS,8aS,8bS)-6-tert-butyl-2,2-dimethyl-3a,5a,8a,8b-tetrahydro-[1,3]dioxolo[4,5-g][1,3]benzoxazol-7-one
  参考文献：
  名称：

  A Chiron Approach to Aminocytitols by Petasis-Borono-Mannich Reaction: Formal Synthesis of (+)-Conduramine E and (−)-Conduramine E

  摘要：

  A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-beta-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.

  DOI：

  10.1021/jo300804d
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 咪唑 、 vitamin B12 、 碘 、 氯化铵 、 三苯基膦 、 锌 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 27.25h， 生成 (4R,4'S,5R,5'S)-2,2,2',2'-tetramethyl-5'-vinyl-[4,4'-bi(1,3-dioxolan)]-5-ol
  参考文献：
  名称：

  A Chiron Approach to Aminocytitols by Petasis-Borono-Mannich Reaction: Formal Synthesis of (+)-Conduramine E and (−)-Conduramine E

  摘要：

  A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-beta-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.

  DOI：

  10.1021/jo300804d

文献信息

• N-Substituted 5-amino-1-hydroxymethyl-cyclopentanetriols: A new family of activity promotors for a G M1 -gangliosidosis related human lysosomal β-galactosidase mutant
  作者：Michael Schalli、Christina Tysoe、Roland Fischer、Bettina M. Pabst、Martin Thonhofer、Eduard Paschke、Tanja Rappitsch、Arnold E. Stütz、Marion Tschernutter、Werner Windischhofer、Stephen G. Withers

  DOI：10.1016/j.carres.2017.03.009

  日期：2017.4

  From 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, a series of highly functionalized (hydroxymethyl)cyclopentanes was easily available. In line with reports by Reymond and Jager on similar structures, these amine containing basic carbasugars are potent inhibitors of beta-D-galactosidases and, for the first time, could be shown to act as pharmacological chaperones for G(M1)-gangliosidosis-associated lysosomal acid beta-galactosidase mutant R201C, thus representing a new structural type of pharmacological chaperones for this lysosomal storage disease. (C) 2017 Elsevier Ltd. All rights reserved.
• (−)-Lytophilippine A: Synthesis of a C1−C18 Building Block
  作者：Annika Gille、Martin Hiersemann

  DOI：10.1021/ol1023008

  日期：2010.11.19

  The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing D-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).