CN103804152B - (2R, 3R)-or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation method of 4-tetraphenyl-2,3-butanediol - Google Patents

(2R, 3R)-or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation method of 4-tetraphenyl-2,3-butanediol Download PDF

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CN103804152B
CN103804152B CN201410053033.2A CN201410053033A CN103804152B CN 103804152 B CN103804152 B CN 103804152B CN 201410053033 A CN201410053033 A CN 201410053033A CN 103804152 B CN103804152 B CN 103804152B
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tetraphenyl
nitrae
isosorbide
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CN103804152A (en
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胡晓允
单自兴
陈东志
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South Central Minzu University
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Abstract

The invention discloses one (2R, 3R)-or (2S, 3S)-1, 4-dimethoxy-1, 1, 4, 4-tetraphenyl-2, the preparation method of 3-butyleneglycol: optical pure tartaric acid diethyl ester is obtained (2R after phenylating, 3R)-or (2S, 3S)-1, 1, 4, 4-tetraphenyl butantetraol, react with sulfur oxychloride and generate (4R, 5R)-or (4S, 5S)-4, the two hexichol chloromethyl cyclic sulfite of 5-, in the presence of a base, methoxyl group is introduced with methyl alcohol generation substitution reaction in appropriate medium, obtained (4R, 5R)-or (4S, 5S)-4, 5-bi-methoxy diphenyl-methyl cyclic sulfite, again in the presence of a base, slough sulfinyl blocking groups in appropriate medium and obtain (2R, 3R)-or (2S, 3S)-1, 4-dimethoxy-1, 1, 4, 4-tetraphenyl-2, 3-butyleneglycol.The method raw material is easy to get, easy and simple to handle, and with low cost.

Description

(2R, 3R)-or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation method of 4-tetraphenyl-2,3-butanediol
Technical field
The present invention relates to C 2the preparation method of Symmetric Chiral glycol, belongs to preparation method's technical field of chipal compounds, specifically discloses one (2R, 3R)-or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation method of 4-tetraphenyl-2,3-butanediol.
Background technology
C 2chiral diol as pure in mapping dinaphthol [(a) Whitesell, J.K.Chem.Rev.1989,89,1581; (b) Brunel, J.M.Chem.Rev.2005,105,857-897; (c) Chen, Y.; Yekta, S.; Yudin, A.K.Chem.Rev.2003,103,3155 – 3212; (d) Periasamy, M.Aldrichim.Acta.2002,35,89.] and TADDOLs [(a) Pellissier, H.Tetrahedron2008,64,10279; (b) Seebach, D.; Beck, A.K.; Heckel A.Angew.Chem.Int.Ed.2001,40,92.] etc. be widely used in asymmetric catalysis synthesis and supramolecular chemistry.The C that tartrate is derivative 2chiral diol (2R, 3R)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, 4-tetraphenyl-2,3-butanediol is as chiral auxiliary(reagent), and especially the protecting group of chirality boric acid ester, is widely used in asymmetric synthesis.[(a)Vahabi,R.;Frey,W.;Pietruszka,J.J.Org.Chem.2013,78,11549.(b)Berg,C.A.;Eichenauer,N.C.;Pietruszka,J.Pure Appl.Chem.2012,84,2339.(c)Fernández,E.;Frey,W.;Pietruszka,J.Synlett2010,1386;(d)Luithle,J.;Pietruszka,J.J.Org.Chem.2000,65,9194.]
(2R, 3R)-and (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, 4-tetraphenyl-2,3-butanediol is by Nakayama andRainier obtained [Nakayama, K. the earliest; Rainier, J.D.Tetrahedron1990,46,4165.]: from Threaric acid ester, through 5 step reactions, target product total recovery is 38%.Wherein crucial step is that the protection and going of tartrate secondary hydroxyl is protected and the program that methylates of tert-hydroxyl, sloughs blocking group and will use reagent D DQ costly and LiAlH 4, methylation reaction is then realized by NaH/MeI system.2008, [Bischop, the M. such as Pietruszk, J.; Cmrecki, V.; Ophoven, V.; Pietruszk, J.Synthesis2008,2488.] this preparation method is improved: instead of expensive poisonous DDQ with cheap inorganic salt and be oxidized, but still will LiAlH be used 4.Recently, our study group has developed boron chemical process preparation (2R, 3R)-and (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol [Authorization Notice No.: CN101921181B]: tartrate and phenyl grignard reagent react obtained chirality 1,1,4,4-tetraphenyl butantetraol, is reacted with boric acid ester and generates chirality spiral shell borate, then methylated by NaH/MeI system, finally obtain (2R with HF/MeOH hydrolysis, 3R)-or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol.Although we avoid oxidation, reducing program at this boron chemical process of research and development, do not use expensive poisonous DDQ, LiAlH 4deng reagent, but still have employed NaH/MeI system and methylate, and be hydrolyzed with HF, in cost and environment, still there is many problems.
Based on above-mentioned condition, the invention provides one with optical pure tartaric acid ester for chiral source, by sulfinyl chiral 1, 1, 4, 2 of 4-tetraphenyl butantetraol, 3-position secondary hydroxyl carries out protecting and go protection, by (4R, 5R)-or (4S, 5S)-4, methoxyl group is introduced in the two hexichol chloromethyl cyclic sulfite of 5-and methyl alcohol generation substitution reaction, avoid traditional NaH/MeI to methylate program, (the 4R obtained, 5R)-or (4S, 5S)-4, 5-bi-methoxy diphenyl-methyl cyclic sulfite removes sulfinyl blocking groups group under finite concentration base catalysis, obtained (2R, 3R)-or (2S, 3S)-1, 4-dimethoxy-1, 1, 4, 4-tetraphenyl-2, 3-butyleneglycol, there is not been reported for this synthetic method.
Summary of the invention
For the deficiencies in the prior art, one has been the object of the present invention is to provide to prepare (2R, 3R) or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, efficient, the convenient method of 4-tetraphenyl-2,3-butanediol.The method raw material is easy to get, easy and simple to handle and with low cost.
Principle of the present invention: phenyl grignard reagent and optical pure tartaric acid diethyl ester are obtained by reacting (2R; 3R)-or (2S, 3S)-1,1; 4; 4-tetraphenyl butantetraol, reacts obtained (4R, 5R)-or (4S with sulfur oxychloride; 5S)-4; the two hexichol chloromethyl cyclic sulfite of 5-, introduces methoxyl group with methyl alcohol generation substitution reaction then, then under base catalysis, sloughs sulfinyl blocking groups obtain target compound.Wherein, (4R, 5R)-or (4S, 5S)-4, the two hexichol chloromethyl cyclic sulfite of 5-can according to previous patent (Dan Zixing, Hu Xiaoyun, patent publication No. CN102603705A) by (2R, 3R)-or (2S, 3S)-1, Isosorbide-5-Nitrae, 4-tetraphenyl butantetraol and sulfur oxychloride react obtained, see embodiment 6 and the embodiment 7 of this patent application.
Technical scheme of the present invention: optical pure tartaric acid diethyl ester is through the obtained (2R of phenylating, 3R)-or (2S, 3S)-1, Isosorbide-5-Nitrae, 4-tetraphenyl butantetraol, obtained (the 4R of regioselective reaction is carried out again with sulfur oxychloride, 5R)-or (4S, 5S)-4,5-pairs of hexichol chloromethyl cyclic sulfites.In the presence of a base, in suitable reaction medium, introduce methoxyl group with methyl alcohol generation substitution reaction; obtained (4R, 5R)-or (4S, 5S)-4; 5-bi-methoxy diphenyl-methyl cyclic sulfite, then under base catalysis, in suitable solvent, slough sulfinyl blocking groups obtain (2R; 3R)-or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1; 1; 4,4-tetraphenyl-2,3-butanediol.
According to the present invention, (2R, 3R)-or (2S, 3S)-1, 4-dimethoxy-1, 1, 4, 4-tetraphenyl-2, the preparation of 3-butyleneglycol is to (2R by sulfinyl, 3R)-or (2S, 3S)-1, 1, 4, 2 of 4-tetraphenyl butantetraol, 3-position secondary hydroxyl carries out protection and de-protected, and by (4R, 5R)-or (4S, 5S)-4, methoxyl group is introduced in the substitution reaction of the two hexichol chloromethyl cyclic sulfite of 5-and methyl alcohol, obtained (4R, 5R)-or (4S, 5S)-4, 5-bi-methoxy diphenyl-methyl cyclic sulfite, avoid NaH/MeI methylation method traditional at present.The going to protect of sulfinyl removes under base catalysis, goes protection process unresolvable tartaric acid chiral skeleton that racemization does not occur at this.
According to the present invention, (4R, 5R)-or (4S, 5S)-4,5-pairs of hexichol chloromethyl cyclic sulfites and methyl alcohol carry out substitution reaction alkali used by Py, NEt 3select Deng in organic bases, alkali is (1-10) with the mol ratio of (4R, 5R)-or (4S, 5S)-4,5-pairs of hexichol chloromethyl cyclic sulfites: 1; Reaction medium is selected in THF, acetonitrile, methyl alcohol.
According to the present invention, (4R, 5R)-or (4S, 5S)-4,5-bi-methoxy diphenyl-methyl cyclic sulfite slough the alkali that uses in the reaction of sulfinyl blocking groups by NaOH, KOH, K 2cO 3, Na 2cO 3middle selection, alkali and (4R, 5R)-or (4S, 5S)-4,5-the mol ratio of bi-methoxy diphenyl-methyl cyclic sulfite be (2-10): 1; Reaction medium is tetrahydrofuran (THF), any one or two or more mixtures in acetonitrile, dimethyl formamide, ethanol, water.
Compared with prior art, advantage of the present invention and beneficial effect are:
(the 2R that the present invention describes, 3R)-and (2S, 3S)-1, 4-dimethoxy-1, 1, 4, 4-tetraphenyl-2, 3-butyleneglycol preparation method is with sulfinyl chiral 1, 1, 4, the secondary hydroxyl of 4-tetraphenyl butantetraol carries out protecting and go protection, with (4R, 5R)-or (4S, 5S)-4, methoxyl group is introduced in the substitution reaction of the two hexichol monochloromethyl cyclic sulfite of 5-and methyl alcohol, obtained (4R, 5R)-or (4S, 5S)-4, 5-bi-methoxy diphenyl-methyl cyclic sulfite, under finite concentration base catalysis, remove sulfinyl blocking groups obtain target compound, go protection process unresolvable tartaric acid chiral skeleton that racemization does not occur at this.The method raw material is easy to get, and relative to current existing preparation method, synthetic route is short, does not use DDQ, LiAlH 4expensive or the toxic reagent with HF etc., and do not need NaH and MeI or Me 2sO 4deng methylating reagent, do not need specific installation, easy and simple to handle and with low cost, there is industrial prospect.
Accompanying drawing explanation
Fig. 1 is (4R, 5R)-4,5-single crystal structure figure of bi-methoxy diphenyl-methyl cyclic sulfite that embodiment 1 step 3 obtains.
Embodiment
Applicant will be described in further detail the inventive method in conjunction with specific embodiments below.
Embodiment 1:(2R, 3R)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation method of 4-tetraphenyl-2,3-butanediol, step is as follows:
Step one: (2R, 3R)-1, Isosorbide-5-Nitrae, the preparation of 4-tetraphenyl butantetraol
The tetrahydrofuran solution of (2R, 3R)-diethyl tartrate is added drop-wise in the tetrahydrofuran solution of the phenyl-magnesium-bromide that stirred of 6 equivalents, after having reacted; use saturated aqueous ammonium chloride cancellation; extracted with diethyl ether, concentrated, by obtaining (2R after silica gel column chromatography; 3R)-1; Isosorbide-5-Nitrae, 4-tetraphenyl butantetraol; yield: 50%, m.p.:149-150 DEG C; [α] d 25=+154.0 (c1.2, CHCl 3); IR (KBr): 3436,3058,2916,1598,1492,1447,1063,698; 1h-NMR (CDCl 3, 300MHz): δ 7.37 – 7.13 (m, 20H, Ar-H); 4.65 (d, J=7.2Hz, 2H, OH) 4.41 (d, J=4.7Hz, 2H, CH); 3.77 (d, J=5.3Hz, 2H, OH). 13c-NMR (CDCl3,75MHz) δ 143.8; 142.7; 134.6; 131.5; 129.3; 128.3; 128.2; 127.9; 127.5; 126.7; 125.5; 81.3,69.7.
Step 2: the preparation of (4R, 5R)-4,5-pairs of hexichol chloromethyl cyclic sulfites
(2R, 3R)-1, Isosorbide-5-Nitrae, 4-tetraphenyl butantetraol and sulfur oxychloride under triethylamine exists (mol ratio is 1:4:8) react 3 hours in THF, and add water stopped reaction, extracted with diethyl ether, and after concentrated, column chromatography obtains white solid, yield: 90%, m.p.:187-189 DEG C, [α] d 20=+12.5 (c0.50, EA). 1h-NMR (300MHz, CDCl 3): δ 7.43-7.49 (m, 4H), 7.27-7.35 (m, 10H), 7.14-7.18 (m, 6H), 6.06 (d, J=1.2Hz), 5.82 (d, J=1.8Hz). 13c-NMR (75MHz, CDCl 3): δ 141.4,140.1,129.2,129.0,128.5,128.2,128.1,127.9,87.5,87.3,78.6.
Step 3: (4R, 5R)-4,5-preparation of bi-methoxy diphenyl-methyl cyclic sulfite
(4R, 5R)-4, the two hexichol chloromethyl cyclic sulfite of 5-and methyl alcohol is (mol ratio is 1:3:3) 70 DEG C of heating after 3 hours in anhydrous THF under pyridine exists, concentrated, be chilled to room temperature and separate out (4R, 5R)-4,5-bi-methoxy diphenyl-methyl cyclic sulfite, yield: 96%, m.p.:126-129 DEG C, [α] d 20=-210 (c1, CH 2cl 2). 1h-NMR (300MHz, CDCl 3): δ 7.46-7.25 (m, 20H), 5.87 (d, J=1.8Hz, 1H), 5.55 (d, J=1.5Hz, 1H), 3.00 (s, 3H), 2.64 (s, 3H). 13c-NMR (75MHz, CDCl 3): δ 134.9,134.1,133.9,133.6,132.5,132.3,132.2,131.9,90.8,88.9,57.9,56.5.
Single crystal data: empirical formula, C30H28O5S; Formula weight, 500.58; Calculateddensity, 1.241g/cm 3; Volume (V), 2679 (3) crystal system, Orthorhombic; Space group, P2 (1) 2 (1) 2 (1); Z=4; Unit cell dimensions, a=9.171 (5), b=16.692 (10), c=17.498 (10), ° β=90 °, α=90, γ=90 °; Absorption coefficient (μ), 0.158mm -1; Index ranges-10≤h≤11 ,-20≤k≤20 ,-21≤l≤21; F (000), 1056; GOF, No. 1.043.CCDC: 979502, its structure is shown in Fig. 1 in accompanying drawing.
Step 4: (2R, 3R)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation of 4-tetraphenyl-2,3-butanediol
(4R, 5R)-4,5-bi-methoxy diphenyl-methyl cyclic sulfite and solid NaOH(mol ratio be 1:3) to be dissolved in the mixed solvent of acetonitrile and water in (acetonitrile: water volume ratio is 6:1), 80 DEG C of reacting by heating 5 hours, then remove reaction solvent, add dilute hydrochloric acid acidifying and separate out (2R, 3R)-Isosorbide-5-Nitrae-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol, yield: 98%, m.p.:78-80 DEG C, [α] d 15=+59.6 (c0.08, CHCl 3), 1h NMR (300MHz, CDCl 3): δ 7.25-7.44 (m, 20H, Ph-H), 4.71 (d, J=3.3Hz, 2H, CH), 3.16 (s, 6H, OCH 3), 2.74 (br, 2H, OH). 13c NMR (75MHz, CDCl 3): δ 142.8,141.5,129.0,128.3,128.1,128.0,127.5,127.7,85.4,71.3,53.7.ESI:477 [M+23].
Embodiment 2:(2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation of 4-tetraphenyl-2,3-butanediol, step is as follows:
Step one and step 2: only change raw material (2R, 3R)-diethyl tartrate into (2S, 3S)-diethyl tartrate, all the other operations, all with embodiment 1, obtain (4S, 5S)-4,5-pairs of hexichol chloromethyl cyclic sulfites.
Step 3: (4S, 5S)-4,5-preparation of bi-methoxy diphenyl-methyl cyclic sulfite
(4S, 5S)-4, the two hexichol chloromethyl cyclic sulfite of 5-and triethylamine (mol ratio is 1:4) are dissolved in anhydrous methanol, and 70 DEG C of heating are after 3 hours, concentrated, be chilled to room temperature and separate out (4S, 5S)-4,5-bi-methoxy diphenyl-methyl cyclic sulfite, yield: 95%, m.p.:125-128 DEG C, [α] d 20=+209 (c1, CH 2cl 2). 1h-NMR (300MHz, CDCl 3): δ 7.46-7.25 (m, 20H), 5.87 (d, J=1.8Hz, 1H), 5.55 (d, J=1.5Hz, 1H), 3.00 (s, 3H), 2.64 (s, 3H). 13c-NMR (75MHz, CDCl 3): δ 134.9,134.1,133.9,133.6,132.5,132.3,132.2,131.9,90.8,88.9,57.9,56.5.
Step 4:(2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation of 4-tetraphenyl-2,3-butanediol
(4S, 5S)-4,5-bi-methoxy diphenyl-methyl cyclic sulfite and K 2cO 3(mol ratio is 1:5) to be dissolved in the mixed solvent of dimethyl formamide and water in (dimethyl formamide: water volume ratio is 9:1), 90 DEG C are heated 7 hours, and then in impouring dilute hydrochloric acid, (2S, 3S)-1 is separated out in acidifying, 4-dimethoxy-1, Isosorbide-5-Nitrae, 4-tetraphenyl-2,3-butyleneglycol, yield: 97%, m.p.:78-80 DEG C, [α] d 15=-59.2 (c0.1, CHCl 3), 1h NMR (300MHz, CDCl 3): δ 7.25-7.44 (m, 20H, Ph-H), 4.71 (d, J=3.3Hz, 2H, CH), 3.16 (s, 6H, OCH3), 2.74 (br, 2H, OH). 13c NMR (75MHz, CDCl 3): δ 142.8,141.5,129.0,128.3,128.1,128.0,127.5,127.7,85.4,71.3,53.7.ESI:477 [M+23].
Specific embodiment described in this specification sheets is only to the explanation for example of the present invention's spirit.Those skilled in the art can make various amendment or supplement or adopt similar mode to substitute to described specific embodiment, but can't depart from spirit of the present invention or surmount the scope that appended claims defines.

Claims (3)

1. one kind (2R, 3R)-or (2S, 3S)-1,4-dimethoxy-1, Isosorbide-5-Nitrae, the preparation method of 4-tetraphenyl-2,3-butanediol: in solvent orange 2 A, under alkali A exists, (4R, 5R)-or (4S, 5S)-4, methoxyl group is introduced in the two hexichol chloromethyl cyclic sulfite of 5-and methyl alcohol generation substitution reaction, obtained (4R, 5R)-or (4S, 5S)-4,5-bi-methoxy diphenyl-methyl cyclic sulfite; Next in solvent B, under alkali B exists, (4R, 5R)-or (4S, 5S)-4,5-bi-methoxy diphenyl-methyl cyclic sulfite is sloughed sulfinyl blocking groups and is obtained (2R, 3R)-or (2S, 3S)-1,4-dimethoxy-1, Isosorbide-5-Nitrae, 4-tetraphenyl-2,3-butanediol;
Described solvent orange 2 A is any one in tetrahydrofuran (THF), acetonitrile, methyl alcohol;
Described solvent B is any one or two or more mixtures in tetrahydrofuran (THF), acetonitrile, dimethyl formamide, ethanol, water;
Described alkali A is pyridine or triethylamine;
Described alkali B is NaOH, KOH, K 2cO 3or Na 2cO 3.
2. preparation method according to claim 1, is characterized in that: described alkali A is (1-10) with the mol ratio of (4R, 5R)-or (4S, 5S)-4,5-pairs of hexichol chloromethyl cyclic sulfites: 1.
3. preparation method according to claim 1, is characterized in that: described alkali B and (4R, 5R)-or (4S, 5S)-4,5-the mol ratio of bi-methoxy diphenyl-methyl cyclic sulfite be (2-10): 1.
CN201410053033.2A 2014-02-17 2014-02-17 (2R, 3R)-or (2S, 3S)-Isosorbide-5-Nitrae-dimethoxy-1, Isosorbide-5-Nitrae, the preparation method of 4-tetraphenyl-2,3-butanediol Expired - Fee Related CN103804152B (en)

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CN102603705A (en) * 2012-03-27 2012-07-25 武汉大学 Preparation method of chiral five-membered ring sulfite with active functional groups on alpha-carbon in substituent

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CN102603705A (en) * 2012-03-27 2012-07-25 武汉大学 Preparation method of chiral five-membered ring sulfite with active functional groups on alpha-carbon in substituent

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Title
Facile Synthesis and Unusual Methanesulfonylation Reaction of (2R,3R)-1,4-Dimethoxy-1,1,4,4-tetrasubstituted-2,3-butanediols;Sankareswaran Srimurugan et al.;《Synthetic Communications》;20070809;第37卷;2483–2490 *
MORRIS J . ROBINS,et al..Nucleic acid related compounds. 66. Improved syntheses of 5"-chloro-5"-deoxy- and 5"-S-aryl(or alky1)-5"-thionucleosides.《Canadian Journal of Chemistry》.1991,第69卷1468-1474. *

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