anti-(3S,5S)-3-hydroxy-5-methyltetrahydrofuran-2-one | 144789-81-1

• 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: anti-(3S,5S)-3-hydroxy-5-methyltetrahydrofuran-2-one
• 英文别名: (3S,5S)-3-Hydroxy-5-methyl-1-oxacyclopentan-2-one；(2S,4S)-2-hydroxy-4-methyl-4-butanolide；Hydroxy-2-methyl-4-γ-butanolid；(3S,5S)-3-hydroxy-5-methyloxolan-2-one
• CAS: 144789-81-1
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: XHMUCGPKDKCFHL-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  anti-(3S,5S)-3-hydroxy-5-methyltetrahydrofuran-2-one 、 4-硝基苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(2S,4S)-2-(4'-nitrobenzyloxy)-4-methyl-4-butanolide
  参考文献：
  名称：

  Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide

  摘要：

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.025
• 作为产物：
  描述：

  N-((14S)-14-hydroxy-14-allyl)acetyloyl-(2R)-bornane-10,2-sultam 在 phosphate buffer 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 43.0h， 生成 anti-(3S,5S)-3-hydroxy-5-methyltetrahydrofuran-2-one
  参考文献：
  名称：

  Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide

  摘要：

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.025

文献信息

• Asymmetric Hydrogenation of 2,4-Dioxo Esters: Selective Synthesis of 2-Hydroxy-4-oxo Esters and Direct Access to Chiral 2-Hydroxy-4-butyrolactones
  作者：Véronique Blandin、Jean-François Carpentier、André Mortreux

  DOI：10.1002/(sici)1099-0690(199908)1999:8<1787::aid-ejoc1787>3.0.co;2-o

  日期：1999.8

  2,4-Dioxoesters 1a–c are selectively converted into optically active 2-hydroxy-4-oxoesters 2a–c by hydrogenation with chiral rhodium-aminophosphane-phosphinite catalysts (82–88% ee) or ruthenium-bisphosphane catalysts (52–67% ee). Direct one-pot hydrogenation of 2,4-dioxoesters 1a–c to 2-hydroxy-4-butyrolactones 4a–c proceeds in high yields; catalytic activities, chemo-, dia-, and enantioselectivities

  2,4-二氧代酯 1a-c 通过手性铑-氨基膦-次膦酸催化剂（82-88% ee）或钌-双膦催化剂（52-67）的氢化反应选择性地转化为光学活性的 2-羟基-4-氧代酯 2a-c % ee）。2,4-二氧代酯 1a-c 直接一锅加氢生成 2-羟基-4-丁内酯 4a-c，收率高；催化活性、化学选择性、渗析选择性和对映选择性在很大程度上取决于底物和催化剂的性质。
• Synthesis and enzyme-catalysed reductions of 2-oxo acids with oxygen containing side-chains
  作者：Gurdip Bhalay、Sarah Clough、Lee McLaren、Andrew Sutherland、Christine L. Willis

  DOI：10.1039/a909677i

  日期：——

  A series of novel 2-oxo esters with protected alcohols at the 3-, 4-, 5-, 6- and 7-positions has been prepared either via coupling of an aldehyde with an organometallic reagent (Zn, In or Cr) or via a one-carbon homologation of the precursor acid. A one-pot dual enzyme system was used to convert the simpler 2-oxo acids (with a single MOM ether at either C-3 or C-4) into enantiopure protected 2,3- and 2,4-dihydroxy acids in good yields, but in the cases of the more complex trisubstituted substrates, significant decomposition occurred. Biotransformations have proved valuable for the enantioselective synthesis of protected 2,6,7-trihydroxyhept-3-enoic acids.

  一系列在3-、4-、5-、6-和7-位带有保护醇的新型2-氧代酯，可以通过醛与有机金属试剂（锌、铟或铬）的耦合反应或通过前驱酸的一碳同系化制备。一种一步法双酶系统被用于将简单的2-氧代酸（在C-3或C-4位上带有单一的MOM醚）转化为高对映纯度的保护2,3-和2,4-二羟基酸，产率良好，但在更复杂的三取代底物情况下，发生了显著的分解。生物转化已被证明在保护的2,6,7-三羟基-3-烯酸的对映选择性合成中具有价值。
• New one pot synthesis of a chiral α-hydroxy-γ-butyrolactone via sequential asymmetric hydrogenation of an α,γ-diketoester
  作者：Véronique Blandin、Jean-François Carpentier、André Mortreux

  DOI：10.1016/s0957-4166(98)00281-x

  日期：1998.8

  The hydrogenation of ethyl 2,4-dioxovalerate in the presence of chiral rhodium or ruthenium catalysts provides direct access to 2-hydroxy-4-methyltetrahydrofuran-2-one 4 with syn:anti ratios of up to 84:16 and with up to 98% and 94% e.e. in the syn and anti form, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective generation of 1,3- and 1,4-dioxy-substituted carbanions by sparteine-assisted deprotonation of chiral precursors: Substrate or reagent control in the synthesis of α,γ- and α,δ-diols
  作者：Hartmut Ahrens、Mario Paetow、Dieter Hoppe

  DOI：10.1016/s0040-4039(00)79084-8

  日期：1992.9

  The deprotonation of a dicarbamate, derived from (S)-butane-1,3-diol, by sec-butyllithium takes an highly diastereoselective, but opposite, direction in the presence of (-)-sparteine and of tetramethylethylenediamine (TMEDA), respectively. The (S)-pentane-1,4-diol derivative shows the same stereochemical preference under both conditions.
• Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide
  作者：Katarzyna Kiegiel、Tomasz Bałakier、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1016/j.tetasy.2004.10.025

  日期：2004.12

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.