(1'S,2'R,5R)-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]dihydrofuran-2-one | 266345-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1'S,2'R,5R)-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]dihydrofuran-2-one
• 英文别名: (5R)-5-[(1R,2R)-1-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxypropyl]oxolan-2-one
• CAS: 266345-89-5
• 化学式: C₁₃H₂₆O₅Si
• 分子量: 290.432
• InChiKey: NRLMTIUEMQGBEL-CKYFFXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (1'S,2'R,5R)-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]dihydrofuran-2-one 在 盐酸 、 sodium periodate 、 锂硼氢 、 叔丁基二甲硅基三氟甲磺酸酯 、 silica gel 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R,2S,3R,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-d-Xylo, β-d-Ribo, β-l-Arabino, and β-l-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols

  摘要：

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.

  DOI：

  10.1021/jo010585v
• 作为产物：
  描述：

  (1'S,4''R,5R)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl]-5H-furan-2-one 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 、 sodium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 (1'S,2'R,5R)-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]dihydrofuran-2-one
  参考文献：
  名称：

  对碰碰糖和亲戚的可变策略。1.立体控制合成的伪β-D-吡喃葡萄糖，伪β-D-吡喃呋喃糖，（伪β-D-吡喃呋喃糖基）胺和（伪β-D-吡喃呋喃糖基）胺。

  摘要：

  由1,2-O-异亚丙基-D-甘油醛合成了四种新颖的手性非外消旋碳糖。基于呋喃和吡咯的2-甲硅烷氧基二烯-分别模拟γ-羟基和γ-氨基丁酸的α，γ-二价阴离子-很好地完成了两种全氧化合物的伪β的合成-D-戊吡喃糖和伪-β-D-木呋喃糖，以及两种“异头”氨基衍生物，（伪-β-D-戊吡喃糖基）胺（1,2,4-三-表-有效胺）和（伪-β- D-二呋喃呋喃糖基）胺。两种连续的，非对映选择性高的碳-碳键形成手法，即乙烯基交联的羟醛加成和分子内羟醛化，被证明对这些结构至关重要。

  DOI：

  10.1021/jo000604l

文献信息

• Variable Strategy toward Carbasugars and Relatives. 1. Stereocontrolled Synthesis of Pseudo-β-<scp>d</scp>-gulopyranose, Pseudo-β-<scp>d</scp>-xylofuranose, (Pseudo-β-<scp>d</scp>-gulopyranosyl)amine, and (Pseudo-β-<scp>d</scp>-xylofuranosyl)amine
  作者：Gloria Rassu、Luciana Auzzas、Luigi Pinna、Lucia Battistini、Franca Zanardi、Lucia Marzocchi、Domenico Acquotti、Giovanni Casiraghi

  DOI：10.1021/jo000604l

  日期：2000.10.1

  "anomeric" amino derivatives, (pseudo-beta-D-gulopyranosyl)amine (1,2,4-tri-epi-validamine) and (pseudo-beta-D-xylofuranosyl)amine. Two sequential, highly diastereoselective carbon-carbon bond-forming maneuvers, i.e., a vinylogous crossed aldol addition and an intramolecular aldolization, proved central to these constructions. The fact that readily available heterocyclic diene scaffolds can be employed in the

  由1,2-O-异亚丙基-D-甘油醛合成了四种新颖的手性非外消旋碳糖。基于呋喃和吡咯的2-甲硅烷氧基二烯-分别模拟γ-羟基和γ-氨基丁酸的α，γ-二价阴离子-很好地完成了两种全氧化合物的伪β的合成-D-戊吡喃糖和伪-β-D-木呋喃糖，以及两种“异头”氨基衍生物，（伪-β-D-戊吡喃糖基）胺（1,2,4-三-表-有效胺）和（伪-β- D-二呋喃呋喃糖基）胺。两种连续的，非对映选择性高的碳-碳键形成手法，即乙烯基交联的羟醛加成和分子内羟醛化，被证明对这些结构至关重要。
• The Utility of Furan-, Pyrrole-, and Thiophene-Based 2-Silyloxy Dienes As Demonstrated by Modular Synthesis of Annonaceous Acetogenin Core Units and Their Pyrrolidine and Thiolane Analogues
  作者：Franca Zanardi、Lucia Battistini、Gloria Rassu、Luciana Auzzas、Luigi Pinna、Lucia Marzocchi、Domenico Acquotti、Giovanni Casiraghi

  DOI：10.1021/jo991568x

  日期：2000.4.1

  diene modules, 2-[(tert-butyldimethylsilyl)oxy]furan (TBSOF), N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP), and 2-[(tert-butyldimethylsilyl)oxy]thiophene (TBSOT) and suitable heteroatom-stabilized carbenium ions. By combining TBSOF, TBSOP, and TBSOT nucleophilic synthons with certain tetrahydrofuran, pyrrolidine, and thiolane acceptors, the construction of varied, adjacently

  我们报告了一种模块化的策略，用于获取无水产乙酸原素的核心单元及其氮和硫类似物，从而产生了巨大的结构多样性。该合成是基于重复性乙烯基加成方案的应用，该方案涉及独特的三联甲硅氧基二烯模块，2-[（叔丁基二甲基甲硅烷基）氧基]呋喃（TBSOF），N-（叔丁氧基羰基）-2-[（叔） -丁基二甲基甲硅烷基）氧基]吡咯（TBSOP）和2-[（叔丁基二甲基甲硅烷基）氧基]噻吩（TBSOT）和合适的杂原子稳定的碳正离子。通过将TBSOF，TBSOP和TBSOT亲核合成子与某些四氢呋喃，吡咯烷和硫杂环戊烷受体结合，可以确保构建与杂色产乙酸原素的核心片段相关的各种相邻相邻的寡杂环基序。首先，通过组装涵盖所有氧，氮和硫杂原子组合（即化合物7-9、13-15和19-21）的18个模型构造的集合，验证了枢轴耦合操纵的可靠性。然后，该统一的方案适用于伪造高级双-四氢呋喃，双-吡咯烷和双-硫杂环戊烷支架，这些支架涵盖了
• Parallel, Stereoselective Syntheses of both Enantiomers of Muricatacin and Their Sulfur and Nitrogen Relatives Using the Silyloxy Diene-Based Methodology
  作者：Gloria Rassu、Luigi Pinna、Pietro Spanu、Franca Zanardi、Lucia Battistini、Giovanni Casiraghi

  DOI：10.1021/jo970205z

  日期：1997.6.1
• Synthesis of a Small Repertoire of Non-Racemic 5a-Carbahexopyranoses and 1-Thio-5a-carbahexopyranoses
  作者：Franca Zanardi、Lucia Battistini、Lucia Marzocchi、Domenico Acquotti、Gloria Rassu、Luigi Pinna、Luciana Auzzas、Vincenzo Zambrano、Giovanni Casiraghi

  DOI：10.1002/1099-0690(200206)2002:12<1956::aid-ejoc1956>3.0.co;2-y

  日期：2002.6
• Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-<scp>d</scp>-Xylo, β-<scp>d</scp>-Ribo, β-<scp>l</scp>-Arabino, and β-<scp>l</scp>-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols
  作者：Gloria Rassu、Luciana Auzzas、Luigi Pinna、Vincenzo Zambrano、Lucia Battistini、Franca Zanardi、Lucia Marzocchi、Domenico Acquotti、Giovanni Casiraghi

  DOI：10.1021/jo010585v

  日期：2001.11.1

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.