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Preparation method of (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butanediol

A kind of technology of tetraphenylbutane erythritol and dimethoxy, applied in the field of preparation of C2 symmetrical chiral diols

Inactive Publication Date: 2018-07-13
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Based on the above situation, the present invention starts from natural tartrate and adopts "one-step method" to synthesize (2R,3R)-1,1,4,4-tetraphenylbutanetetraol, through (2R,3R)-1,1, Regioselective 2,3-Dimethylation of 4,4-Tetraphenylbutanetetraol with NaH and Methylating Reagents to Realize (2R,3R)-1,1,4,4-Tetraphenylbutane Methylation of the 2,3-position secondary hydroxyl group of the tetraol while leaving the 1,4-position tertiary hydroxyl group unaffected, leading to efficient preparation of (2R,3R)-2,3-dimethoxy in 43% overall yield base-1,1,4,4-tetraphenyl-1,4-butanediol, the synthesis method has not been reported

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1: A preparation method of (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butanediol, the steps are as follows:

[0015] Step 1: Preparation of (2R,3R)-1,1,4,4-tetraphenylbutanetetraol

[0016] Add (2R,3R)-diethyl tartrate solution in tetrahydrofuran dropwise to 6 equivalents of phenylmagnesium bromide in tetrahydrofuran solution. After the reaction is completed, quench with saturated ammonium chloride aqueous solution, extract with ether, concentrate, and remove from silica gel (2R,3R)-1,1,4,4-Tetraphenylbutanetetraol was obtained after column chromatography, yield: 48%, m.p.: 149-150°C; [α] D 25 =+154.0(c 1.2, CHCl 3 );IR(KBr):3436,3058,2916,1598,1492,1447,1063,698; 1 H-NMR (CDCl 3 ,300MHz): δ7.37–7.13(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). 13 C-NMR (CDCl3, 75 MHz) δ 143.8; 142.7; 134.6; 131.5; 129.3; 128.3; 128.2; 127.9; 127.5;

[0017] Step 2: Preparation of (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butaned...

Embodiment 2

[0019] Example 2: A preparation method of (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butanediol, the steps are as follows:

[0020] Step 1: Preparation of (2R,3R)-1,1,4,4-tetraphenylbutanetetraol

[0021] Add (2R,3R)-diethyl tartrate solution in tetrahydrofuran dropwise to 6 equivalents of phenylmagnesium bromide in tetrahydrofuran solution. After the reaction is completed, quench with saturated ammonium chloride aqueous solution, extract with ether, concentrate, and remove from silica gel (2R,3R)-1,1,4,4-Tetraphenylbutanetetraol was obtained after column chromatography, yield: 48%, m.p.: 149-150°C; [α] D 25 =+154.0(c 1.2, CHCl 3 );IR(KBr):3436,3058,2916,1598,1492,1447,1063,698; 1 H-NMR (CDCl 3 ,300MHz): δ7.37–7.13(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). 13 C-NMR (CDCl3, 75 MHz) δ 143.8; 142.7; 134.6; 131.5; 129.3; 128.3; 128.2; 127.9; 127.5;

[0022]Step 2: Preparation of (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butanedi...

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PUM

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Abstract

The invention relates to a preparation method of C2 symmetric chiral diol, and belongs to the field of chiral compound preparation chemistry. The invention particularly discloses a preparation methodof (2R3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butanediol, which comprises the steps of performing phenylating on natural diethyl tartrate to prepare (2R,3R)-1,1,4,4-tetraphenyl butantetraol; at a certain temperature and in an appropriate reaction medium, carrying out high-regioselectivity 2,3-dimethylation reaction on the (2R,3R)-1,1,4,4-tetraphenyl butantetraol, with NaH and a methylating agentto obtain the (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butanediol. The raw materials of the method are easy to get, the method is simple and convenient to operate, and low in cost.

Description

technical field [0001] The present invention relates to a C 2 The invention discloses a method for preparing symmetrical chiral diols, which belongs to the field of preparation chemistry of chiral compounds, and specifically discloses a (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1 , The preparation method of 4-butanediol. Background technique [0002] C 2 Chiral diols such as enantiopure binaphthols [(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. have been widely used in asymmetric synthesis reactions and supramolecular chemistry . tartaric acid derived C 2 The chiral diol (2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenyl-1,4-butanediol is used as a chiral host in chiral supramolecular ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/178
CPCC07B2200/07C07C41/16C07C43/1785
Inventor 胡晓允尹忠友单自兴
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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