An NMR Study on Diacetonefructose

doi:10.11938/cjmr20162526

Abstract

Abstract: 2,3:4,5-bis-O-(1-methyl ethylidene)-β-D-fructopyranose is also called diacetonefructose, which is an important intermediate for drug synthesis, and contains chiral carbon atoms. In this study, one-dimensional (i.e., ¹H NMR, ¹³C NMR and DEPT135) and two-dimensional (i.e., ¹H-¹³C HMBC, ¹H-¹³C HSQC, ¹H-¹H COSY and NOESY) NMR methods were used to elucidate the structure of this compound. The ¹H and ¹³C NMR chemical shifts of the compound were assigned. Theoretical calculation was used to confirm the correctness of the stereochemistry configuration deduced from the NMR data.

Key words: liquid-state NMR, chemical shift assignment, theoretical calculation, diacetonefructose

CLC Number:

O482.53

SUN Wei, SHE Meng-yao, ZONG Chun-lei, GAO Xiang, GUO Juan. An NMR Study on Diacetonefructose[J]. Chinese Journal of Magnetic Resonance, 2017, 34(3): 329-337.

References

[1] SAYYEDEH S P, SAYYED M H, MEHDI S. Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives:Investigation of kinetics and mechanism[J]. Chinese J Catal, 2015, 36(5):757-763.
[2] MARIA R B, LAURA D L, STEFANIA F, et al. Carbonic anhydrase inhibitors:Design, synthesis and structural characterization of new heteroaryl-N-carbonylbenzenesulfonamides targeting druggable human carbonic anhydrase isoforms[J]. Eur J Med Chem, 2015, 102(18):223-232.
[3] ROSARIA G, STEFANIA F, STEFANO A, et al. Synthesis and evaluation of pharmacological profile of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(¹H)-sulfonamides[J]. Bioorg Med Chem, 2009, 17(10):3659-3664.
[4] CHEN X L. Topiramate tablets, phenobarbital, valproate treatment of pediatric epilepsy comparison[J]. Chinese J Clin Ration Drug Use, 2015, 8(3C):67-68. 陈秀莲. 苯巴比妥、托吡酯片、丙戊酸钠治疗小儿癫痫的疗效比较[J]. 临床合理用药, 2015, 8(3C):67-68.
[5] SADAYUKI A, TAKEHIKO W, YOSHIHISA I. Microenvironmental polarity control of electron-transfer photochirogenesis. enantiodifferentiating polar addition of 1,1-diphenyl-1-alkenes photosensitized by saccharide naphthalenecarboxylates[J]. J Am Chem Soc, 2003, 125(10):3008-3027.
[6] PARR R G, YANG W. Density functional theory of atoms and molecules[M]. New York:Oxford University Press, 1989.
[7] BECKE A D. Density-functional thermochemistry. Ⅲ. The role of exact exchange[J]. J Chem Phys, 1993, 98(7):5648-5652.
[8] DITCHFIELD R, HEHRE W J, POPLE J A. Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules[J]. J Chem Phys, 1971, 54(2):724-728.
[9] FRISCH M J, TRUCKS G W, SCHLEGEL H B, et al. Gaussian 09[M]. Wallingford:Gaussian, Inc., 2009.
[10] SUN W, WEI Y F, BAI Y J, et al. An NMR study of α-mangostin[J]. Chinese J Magn Reson, 2008, 25(2):257-264. 孙伟, 魏永锋, 白银娟, 等. α-山竹黄酮的NMR研究[J]. 波谱学杂志, 2008, 25(2):257-264.
[11] SAMUEL O N, WU W N, BRUCE E M. Synthesis of hydroxylated derivatives of topiramate, a novel antiepileptic drug based on d-fructose:Investigation of oxidative metabolites[J]. Carbohyd Res, 1997, 304(1):29-38.
[12] JOCHEN K, THOMAS Z. Synthesis of spirofused carbohydrate-oxazoline based palladium(Ⅱ) complexes[J]. Carbohyd Res, 2015, 411(26):56-63.
[13] XU C L, ZHENG Y N. Studies on the structural identification of new flavonolglycoside of salix raddeana laksc[J] Chinese J Ana l Chem, 2005, 33(9):1311-1314. 许传莲, 郑毅男. 大黄柳叶中新黄酮苷的结构鉴定[J]. 分析化学, 2005, 33(9):1311-1314.
[14] XU H, LI Y L, TIAN H C, et al. Preparation and chemical structure identification of methylated metabolites of salvianolic acid A[J]. Chinese J Anal Chem, 2014, 42(1):65-70. 许卉, 李艳丽, 田红翠, 等. 丹酚酸A甲基结合代谢物的制备与结构鉴定[J]. 分析化学, 2014, 42(1):65-70.
[15] CHAI J, WANG X, LI H M, et al. A Two-dimensional NMR study on steroid glycosides extracted from trillium tschonoskii[J]. Chinese J Magn Reson, 2015, 32(1):105-115. 柴江, 王欣, 李慧敏, 等. 延龄草中2个甾体皂苷的2D NMR研究[J]. 波谱学杂志, 2015, 32(1):105-115.
[16] YUAN K, JIA A, LV J L, et al. Structural identification of new C-glycosylflavones from mimosa pudica[J]. Chinese J Anal Chem, 2007, 35(5):739-742. 袁珂, 贾安, 吕洁丽, 等. 含羞草中新黄酮碳苷的结构鉴定[J]. 分析化学, 2007, 35(5):739-742.
[17] REN F Z, CHEN S H, ZHANG X X, et al. Structure analysis of an oligosaccharide isolated from bixo orel lana by NMR spectroscopy[J]. Chinese J Magn Reson, 2011, 28(1):160-167. 任风芝, 陈书红, 张雪霞, 等. 胭脂树低聚糖的结构分析[J]. 波谱学杂志, 2011, 28(1):160-167.