(2R,3R)-2,3-二甲氧基-1,1,4,4-四苯基-1,4-丁二醇的一种实用制备方法（英文）
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摘要
基于(2R,3R)-1,1,4,4-四苯基丁四醇的区域选择性2,3-二甲基化反应,建立了一种制备C_2手性二醇即(2R,3R)-2,3-二甲氧基-1,1,4,4-四苯基-1,4-丁二醇的实用方法.结果表明:与文献相比,该合成避免了酸的使用,减少了多取代THF衍生物的生成,提高了产率,不仅是制备(2R,3R)-2,3-二甲氧基-1,1,4,4-四苯基-1,4-丁二醇的便捷方法,也为(2R,3R)-1,1,4,4-四取代丁四醇的区域选择性衍生化提供了重要信息.
A practical approach to(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol,a C_2 chiral diol,was developed based on highly regioselective 2,3-methylation of(2R,3R)-1,1,4,4-tetraphenylbutaneol with MeI/NaH. The results indicated that compared with the literature,this procedure avoided the treatment with acid,reduced the generation of poly-substituted THF derivative,and increased the yield. This report not only provided a practical approach to prepare(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol,but also presented a significant reference for the regioselective derivatization of(2R,3R)-1,1,4,4-tetra-substituted butanetetraols.
A practical approach to(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol,a C_2 chiral diol,was developed based on highly regioselective 2,3-methylation of(2R,3R)-1,1,4,4-tetraphenylbutaneol with MeI/NaH. The results indicated that compared with the literature,this procedure avoided the treatment with acid,reduced the generation of poly-substituted THF derivative,and increased the yield. This report not only provided a practical approach to prepare(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol,but also presented a significant reference for the regioselective derivatization of(2R,3R)-1,1,4,4-tetra-substituted butanetetraols.
引文
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[3] SEEBACH D,BECK A K,BICHSEL H U,et al.Preparation and characterization of new C2- and C1-Symmetric Nitrogen, oxygen, phosphorous, and sulfur derivatives and analogs of TADDOL. Part III [J]. Helvetica Chimica Acta, 2012, 95(8): 1303-1324.
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[10] HU X, SHAN Z, PENG X, et al. Convenient access tosterically hindered C2 chiral 2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols: Intramolecular selective 1,4-cyclocondensation of(2R,3R)- and(2S,3S)-1,1,4,4-tetraphenylbutanetetraols [J]. Tetrahedron: Asymmetry, 2009, 20(21): 2474-2478.
[11] SHAN Z, HU X, ZHOU Y, et al. Selective 1,3-cycloboronation ofenantiopure 1,1,4,4-tetrasubstituted butanetetraols: Versatile preparation, structural characterization, and properties of chiral cyclic boron-containing bifunctional lewis acids [J]. Tetrahedron: Asymmetry,2009, 20(12):1445-1450.
[12] HU X , SHAN Z, SONG S. A novel, high-yielding approach to achiral inducer:(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol [J]. Tetrahedron: Asymmetry, 2014, 25(6/7): 503-506.
[13] XIE J S, HU X Y, SHAN Z X, et al. A straightforward and practical approach tochiral inducer:(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl butane-2,3-diol [J]. Aust J Chem, 2015, 68(6): 995-998.
[14] HU X,SHAN Z,SOLOSHONOK V A.First experimental evidence of anintramolecular H bond between aliphatic Cl and aromatic C-H [J]. Cryst Growth Des, 2012, 12(12): 33-36.
[15] BERG C A, EICHENAUER N C, PIETRUSZKA J.(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates [J]. Pure Appl Chem, 2012, 84: 2339-2416.
[16] PURDIE T, YOUNG C R CXIV.Optically active derivatives of l-methoxy- and d-dimethoxy-succinic acids [J]. J Chem Soc Tran, 1910, 97: 1524-1536.
[2] SEEBACH D, BECK A K, HECKEL A. TADDOLs, their derivatives, and TADDOL analogues:Versatile chiral auxiliaries [J]. Angew Chem Int Ed Engl, 2001, 40(1): 92-138.
[3] SEEBACH D,BECK A K,BICHSEL H U,et al.Preparation and characterization of new C2- and C1-Symmetric Nitrogen, oxygen, phosphorous, and sulfur derivatives and analogs of TADDOL. Part III [J]. Helvetica Chimica Acta, 2012, 95(8): 1303-1324.
[4] WHITESELL J K.C2 symmetry and asymmetric induction [J]. Chem Rev, 1989, 89(7): 1581-1590.
[5] BARTON B, HOSTEN E C, POHL P L. Host(-)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol and guests aniline, N-methylaniline, and N, N-dimethylaniline: A selectivity study [J]. Aust J Chem, 2018, 71(3): 133-141.
[6] BARTON B, DORFLING S L, HOSTEN E C, et al. Host compounds(+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol(TETROL) and(2R,3R)-(-)-2, 3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol(dmt) with guests o-, m- and p-toluidine: A comparative investigation [J]. Tetrahedron, 2018, 74(22): 2754-2761.
[7] BARTON B, HOSTEN E C, POHL P L. Discrimination between o-xylene, m-xylene, p-xylene and ethylbenzene by host compound(R,R)-(-)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol [J]. Tetrahedron, 2016, 72(49): 8099-8105.
[8] TODA F, TANAKA K, STEIN Z, et al. Structure and inclusion characteristics of(R,R)-(-)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol [J]. J Chem Soc Perkin Trans,1993, 2: 2359-2361.
[9] SHAN Z X, HU X, ZHOU Y, et al. A convenient approach to C2-chiral 1,1,4,4-tetrasubstituted butanetetraols: Direct alkylation or arylation of enantiomerically pure diethyl tartrates [J]. Helvetica Chimica Acta, 2010, 93(3): 497-503.
[10] HU X, SHAN Z, PENG X, et al. Convenient access tosterically hindered C2 chiral 2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols: Intramolecular selective 1,4-cyclocondensation of(2R,3R)- and(2S,3S)-1,1,4,4-tetraphenylbutanetetraols [J]. Tetrahedron: Asymmetry, 2009, 20(21): 2474-2478.
[11] SHAN Z, HU X, ZHOU Y, et al. Selective 1,3-cycloboronation ofenantiopure 1,1,4,4-tetrasubstituted butanetetraols: Versatile preparation, structural characterization, and properties of chiral cyclic boron-containing bifunctional lewis acids [J]. Tetrahedron: Asymmetry,2009, 20(12):1445-1450.
[12] HU X , SHAN Z, SONG S. A novel, high-yielding approach to achiral inducer:(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol [J]. Tetrahedron: Asymmetry, 2014, 25(6/7): 503-506.
[13] XIE J S, HU X Y, SHAN Z X, et al. A straightforward and practical approach tochiral inducer:(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl butane-2,3-diol [J]. Aust J Chem, 2015, 68(6): 995-998.
[14] HU X,SHAN Z,SOLOSHONOK V A.First experimental evidence of anintramolecular H bond between aliphatic Cl and aromatic C-H [J]. Cryst Growth Des, 2012, 12(12): 33-36.
[15] BERG C A, EICHENAUER N C, PIETRUSZKA J.(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates [J]. Pure Appl Chem, 2012, 84: 2339-2416.
[16] PURDIE T, YOUNG C R CXIV.Optically active derivatives of l-methoxy- and d-dimethoxy-succinic acids [J]. J Chem Soc Tran, 1910, 97: 1524-1536.
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