(3S,4S,5S)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone | 110612-43-6

• 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: (3S,4S,5S)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
• 英文别名: 3-butyl-4-hydroxy-5-methyl-(3S,4S,5S)-tetrahydro-2-furanone；epi-blastmycinolactol；α-n-Butyl-β-hydroxy-γ-valerolacton；(3S,4S,5S)-3-butyl-4-hydroxy-5-methyloxolan-2-one
• CAS: 110612-43-6
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: LLALEXXCKCFLES-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone 、 异戊酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到4-butyl-2-methyl-5-oxo-(2S,3S,4S)-tetrahydro-3-furanyl 3-methylbutanoate
  参考文献：
  名称：

  三取代 γ-丁内酯立体选择性合成的灵活简单路线：(+)-芽生霉素及其类似物的全合成

  摘要：

  通过 Sharpless 不对称环氧化和与二丁基铜锂的区域选择性开环反应作为引入所需烷基链的关键步骤，设计了一种灵活的立体选择性合成三取代 γ-丁内酯（即 (+)-blastomycinone 及其类似物）的路线。

  DOI：

  10.1055/s-2004-829173
• 作为产物：
  描述：

  methyl (E)-pent-3-enoate 在 potassium osmate(VI) 正丁基锂 、 β-1,4-bis-(dihydroquinidinyl)phthalazine 、 potassium carbonate 、 二异丙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 正己烷 、 水 、 叔丁醇 为溶剂， 反应 38.5h， 生成 (3S,4S,5S)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
  参考文献：
  名称：

  通过全合成阐明花环产乙酸原（+）-蒙特克里斯汀的立体结构

  摘要：

  完成了ent -5- epi- montecristin（1a）和（-）-montecristin（1b）的总合成。化合物1a和1b的立体中心是通过反式构型的β，γ-不饱和酯6的不对称二羟基化而建立的（→ 4，至多80％ee；方案3；改进的程序，至多94％ee：方案7）和56（→ 55，97％ee的：方案9），而立体ç C键从carbocuprations干48 → 49和50 → 51（方案9）。用PPh 3和DEAD处理羟基内酯27（方案7）， 3a（方案12）和3b（方案13），我们发现无外消旋的脱水作用生成丁烯内酯26，无差向异构化的脱水作用生成丁烯内酯2a和2b 。有关的[ α ] d合成的值 1A和1B到[ α ] d天然（+）的值- montecristin，测定其侧链立体中心的绝对构型为[R 。

  DOI：

  10.1039/b002905j

文献信息

• Total Syntheses of (−)-Grandinolide and (−)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyltrans-3-Pentenoate: Elucidation of the Stereostructure of (−)-Sapranthin
  作者：Christian Harcken、Reinhard Brückner、Elisabeth Rank

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2342::aid-chem2342>3.0.co;2-q

  日期：1998.11.2

  Methyl trans-3-pentenoate (7) was converted into the cis-substituted gamma-lactone 8 in a single step with 78 % ee. The derived enolate dilithio-8 was alkylated trans-selectively with primary iodoalkanes. with 1-iodobutane dilithio-8 afforded, after esterification with isovaleroyl chloride, the epi-blast mycinone 9, Dilithio-8 gave (-)-grandinolide (11) with 1-iodo-19-phenylnonadecane (20), A third trans-selective alkylation of dilithio-8 was undertaken with 16-iodo-1.5-hexadecadiene-7,9-diyne (21). This gave the gamma-lactone 12. which had the published relative configuration of (-)-sapranthin but different spectroscopic data, When the OH group of lactone 8 was inverted (to hydroxylactone 40) and the derived enolate dilithio-40 alkylated with iodide 21, lactone 41 resulted, Its H-1 and C-13 NMR spectra and the sign and value of optical rotation coincide with the data of natural sapranthin, These findings establish that (-)-sapranthin possesses the relative and absolute configuration of stereoformula 41. The synthesis of iodide 21 was performed via the dienoic carboxylic ester trans-23 which stemmed from the Claisen-Ireland rearrangement (27 --> 28/29)/esterification (28/29 --> 26)/Cope rearrangement (26 - 23) sequence shown in Scheme 5.
• Synthesis of Optically Active Butenolides andγ-Lactones by the Sharpless Asymmetric Dihydroxylation ofβ,γ-Unsaturated Carboxylic Esters
  作者：Christian Harcken、Reinhard Brückner

  DOI：10.1002/anie.199727501

  日期：1997.1.7
• Kishikawa, Keiki; Sankhavasi, Wongsiri; Yamamoto, Makoto, Synthetic Communications, 1990, vol. 20, # 15, p. 2339 - 2347
  作者：Kishikawa, Keiki、Sankhavasi, Wongsiri、Yamamoto, Makoto、Kohmoto, Shigeo、Yamada, Kazutoshi

  DOI：——

  日期：——
• Stereoselective synthesis of (±)-blastmycinome and formal total synthesis of antimycin A3
  作者：Tadashi Nakata、Mineo Fukui、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)87970-8

  日期：1983.1
• High diastereoselective aldol reactions of cobalt-complexed and uncomplexed propynals with an O-silyl ketene O,S-acetal: highly stereoselective total syntheses of (.+-.)-blastmycinone and its three diastereoisomers from 3-(trimethylsilyl)propynal
  作者：Chisato Mukai、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1021/jo00063a008

  日期：1993.5

  Total syntheses of (+/-)-blastmycinone (2) and its three diastereoisomers (3-5) are described. The syntheses involve highly stereoselective aldol reactions of cobalt-complexed propynal 6 and uncomplexed propynal 7 with O-silyl ketene O,S-acetal 8, which possesses an n-butyl tether, under Mukaiyama conditions. (+/-)-Blastmycinone (2) and its 2-epimer 3 were stereoselectively synthesized through chelation-controlled reduction, whereas (+/-)-3-epi- and 4-epiblastmycinone (5 and 4) were obtained in a highly stereocontrolled manner with bromolactonization as a key step.