(S)-5-((S)-1,2-dihydroxyethyl)dihydrofuran-2(3H)-one | 56405-80-2

• 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: (S)-5-((S)-1,2-dihydroxyethyl)dihydrofuran-2(3H)-one
• 英文别名: 2,3-dideoxy-L-threo-hexono-1,4-lactone；(5S)-5-[(1S)-1,2-dihydroxyethyl]oxolan-2-one
• CAS: 56405-80-2
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: WKCBOODKPXKQAC-WHFBIAKZSA-N

物化性质

• 沸点：
  410.9±15.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-((S)-1,2-dihydroxyethyl)dihydrofuran-2(3H)-one 在 咪唑 、 迭氮酸 、 borane dimethyl sulphide complex 、 20% palladium hydroxide on carbon 、 氢气 、 sodium methylate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 20.0 ℃ 、448.17 kPa 条件下， 反应 49.0h， 生成 (2R,3S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  A convenient formal synthesis of (2S,3S)-3-hydroxy pipecolic acid

  摘要：

  A convenient synthesis of (2S,3S)-3-hydroxy pipecolic acid starting from inexpensive and easily available L-(+)-tartaric acid has been described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.023
• 作为产物：
  描述：

  L-古洛糖酸-gamma-内酯 在 palladium on activated charcoal 氢溴酸 、 氢气 、 sodium hydrogensulfite 、 溶剂黄146 、 silver(l) oxide 作用下， 以 水 、 乙酸乙酯 、 异丙醇 为溶剂， 30.0 ℃ 、202.65 kPa 条件下， 反应 12.0h， 生成 (S)-5-((S)-1,2-dihydroxyethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Vitamin C and isovitamin C derived chemistry. 4. Synthesis of some novel furanone chirons

  摘要：

  DOI：

  10.1021/jo00306a008

文献信息

• A Stereoselective Synthesis of Nonracemic (+)-Desoxoprosophylline by a Tandem Wittig [2+3]-Cycloaddition Reaction
  作者：Claus Herdeis、Joachim Telser

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1407::aid-ejoc1407>3.0.co;2-t

  日期：1999.6

  L-Ascorbic acid serves as chiral starting material for the synthesis of (+)-desoxoprosophylline. The synthetic pathway includes the formation of an O-protected 5-azido-2,3-dideoxysugar which is subjected to a tandem Wittig [2+3]-cycloaddition reaction, leading to the heterocyclic core unit of (+)-prosophylline. Stereoselective hydrogenation and chain elongation yields the desired alkaloid.

  L-抗坏血酸用作合成 (+)-desoxoprosophylline 的手性原料。合成途径包括形成 O-保护的 5-叠氮基-2,3-双脱氧糖，该糖经过串联 Wittig [2+3]-环加成反应，生成 (+)-prosophylline 的杂环核心单元。立体选择性氢化和链延长产生所需的生物碱。
• Enantiodivergent synthesis of muricatacin related lactones from d-xylose based on the latent symmetry concept: preparation of two novel cytotoxic (+)- and (−)-muricatacin 7-oxa analogs
  作者：Velimir Popsavin、Ivana Krstić、Mirjana Popsavin、Bojana Srećo、Goran Benedeković、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.tet.2006.09.054

  日期：2006.11

  Enantiodivergent formal synthesis of (+)- and (−)-muricatacins from d-xylose has been accomplished through utilization of the latent plane of symmetry present in the starting monosaccharide. This approach was extended to the preparation of two novel (+)- and (−)-muricatacin 7-oxa analogs (2 and ent-2, respectively), which showed in vitro antitumor activity toward some human malignant cells. The analog

  通过利用存在于起始单糖中的对称性潜平面，已完成了由d-木糖对映体形式的（+）-和（-）-穆里卡他星的对映体形式合成。该方法扩展到制备两种新颖的（+）-和（-）-多卡他霉素7-oxa类似物（分别为2和ent - 2），它们显示出对某些人类恶性细胞的体外抗肿瘤活性。类似物ent - 2对K562细胞系显示出强大的抗增殖活性，效力比标准细胞毒剂阿霉素高36倍。化合物2然而，它对HL-60细胞显示出强大的细胞毒活性，相对于参比化合物，其效力高17倍以上。
• Enantiopure hydroxylactones from d-xylose. A novel approach to the enantiodivergent synthesis of (+)- and (−)-muricatacin suitable for the preparation of 7-oxa analogues
  作者：Velimir Popsavin、Ivana Krstić、Mirjana Popsavin

  DOI：10.1016/j.tetlet.2003.09.168

  日期：2003.12

  A new route towards enantiopure hydroxylactones 3 and ent-3, the final chiral precursors in an enantiodivergent synthesis of (+)- and (−)-muricatacin, has been developed starting from d-xylose.

  从d-木糖开始，已开发出一种新的途径，以对映体纯的羟基内酯3和ent - 3为对映体合成（+）-和（-）-多卡他霉素的最终手性前体。
• Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-<scp>l</scp>-<i>erythro(threo)</i>-hexono-1,4-lactone and 2-Deoxyapiolactone
  作者：Jeewoo Lee、Nancy E. Lewin、Peter Acs、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm960525v

  日期：1996.1.1

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.
• VEKEMANS, JOZEF A. J. M.;DAPPERENS, CORNELIS W. M.;CLAESSEN, RON;KOTEN, A+, J. ORG. CHEM., 55,(1990) N9, C. 5336-5344
  作者：VEKEMANS, JOZEF A. J. M.、DAPPERENS, CORNELIS W. M.、CLAESSEN, RON、KOTEN, A+

  DOI：——

  日期：——