bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate

Base Information

• Chemical Name: bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate
• CAS No.: 105365-13-7
• Molecular Formula: C₃₂H₄₄O₇
• Molecular Weight: 540.697

Synonyms:

Chemical Property of bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate

There total 20 articles about bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl 3,5-dihydoxy-2,4-dimethylpentanoate (105365-06-8) → bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate (105365-13-7,133097-14-0)

Guidance literature:

Multi-step reaction with 18 steps

1: Amberlyst 15 / methanol / 68 h

2: 96 percent / LiAlH₄ / diethyl ether / a) -20 deg C, 3 h, b) r.t., 1.5 h

3: 1) 55percent NaH, 2) Et₄NI / 1) hexane, DMF, r.t., 1 h, 2) r.t., 16 h

4: 92 percent / conc. HCl / tetrahydrofuran / 6 h / Ambient temperature

5: 94 percent / imidazole, 4 Angstroem molecular sieves / dimethylformamide / 23 h / Ambient temperature

7: 53 percent / Zn(BH₄)2 / diethyl ether / 7 h / -78 °C

8: 93 percent / H₂ / 10percent Pd/C / ethyl acetate / 7 h / Ambient temperature

9: 92 percent / camphorsulfonic acid / 6 h / Ambient temperature

10: 99 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

12: (i-Pr)2NH / tetrahydrofuran / 1 h / -78 °C

13: 67 percent / conc. HCl / tetrahydrofuran / 2.5 h / Ambient temperature

14: 96 percent / imidazole, molecular sieves 4 Angstroem / dimethylformamide / 7 h / Ambient temperature

15: 97 percent / camphorsulfonic acid / 5 h

16: 99 percent / Bu₄NF / tetrahydrofuran / 7 h / Ambient temperature

18: tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; Amberlyst 15; zinc(II) tetrahydroborate; 4 A molecular sieve; camphor-10-sulfonic acid; tetraethylammonium iodide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19900730821

Reference yield:

1-methyl hydrogen (3S,2R,4S)-3-hydroxy-2,4-dimethylglutarate (89329-05-5) → bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate (105365-13-7,133097-14-0)

Guidance literature:

Multi-step reaction with 19 steps

1: BH₃*Me₂S / a) THF, -10 deg C, 1.5 h, b) rt, 3h

2: Amberlyst 15 / methanol / 68 h

3: 96 percent / LiAlH₄ / diethyl ether / a) -20 deg C, 3 h, b) r.t., 1.5 h

4: 1) 55percent NaH, 2) Et₄NI / 1) hexane, DMF, r.t., 1 h, 2) r.t., 16 h

5: 92 percent / conc. HCl / tetrahydrofuran / 6 h / Ambient temperature

6: 94 percent / imidazole, 4 Angstroem molecular sieves / dimethylformamide / 23 h / Ambient temperature

8: 53 percent / Zn(BH₄)2 / diethyl ether / 7 h / -78 °C

9: 93 percent / H₂ / 10percent Pd/C / ethyl acetate / 7 h / Ambient temperature

10: 92 percent / camphorsulfonic acid / 6 h / Ambient temperature

11: 99 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

13: (i-Pr)2NH / tetrahydrofuran / 1 h / -78 °C

14: 67 percent / conc. HCl / tetrahydrofuran / 2.5 h / Ambient temperature

15: 96 percent / imidazole, molecular sieves 4 Angstroem / dimethylformamide / 7 h / Ambient temperature

16: 97 percent / camphorsulfonic acid / 5 h

17: 99 percent / Bu₄NF / tetrahydrofuran / 7 h / Ambient temperature

19: tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; Amberlyst 15; zinc(II) tetrahydroborate; dimethylsulfide borane complex; 4 A molecular sieve; camphor-10-sulfonic acid; tetraethylammonium iodide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19900730821

Reference yield:

methyl (2R,3S,4R)-3,5-(isopropylidenedioxy)-2,4-dimethylpentanoate (105365-07-9) → bis(2,6-dimethylphenyl) (2S,3S,4S,5S,6S,7R,8R)-5,7-(isopropylidenedioxy)-2,4,6,8-tetramethyl-nonane-1,9-dioate (105365-13-7,133097-14-0)

Guidance literature:

Multi-step reaction with 17 steps

1: 96 percent / LiAlH₄ / diethyl ether / a) -20 deg C, 3 h, b) r.t., 1.5 h

2: 1) 55percent NaH, 2) Et₄NI / 1) hexane, DMF, r.t., 1 h, 2) r.t., 16 h

3: 92 percent / conc. HCl / tetrahydrofuran / 6 h / Ambient temperature

4: 94 percent / imidazole, 4 Angstroem molecular sieves / dimethylformamide / 23 h / Ambient temperature

6: 53 percent / Zn(BH₄)2 / diethyl ether / 7 h / -78 °C

7: 93 percent / H₂ / 10percent Pd/C / ethyl acetate / 7 h / Ambient temperature

8: 92 percent / camphorsulfonic acid / 6 h / Ambient temperature

9: 99 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

11: (i-Pr)2NH / tetrahydrofuran / 1 h / -78 °C

12: 67 percent / conc. HCl / tetrahydrofuran / 2.5 h / Ambient temperature

13: 96 percent / imidazole, molecular sieves 4 Angstroem / dimethylformamide / 7 h / Ambient temperature

14: 97 percent / camphorsulfonic acid / 5 h

15: 99 percent / Bu₄NF / tetrahydrofuran / 7 h / Ambient temperature

17: tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; 4 A molecular sieve; camphor-10-sulfonic acid; tetraethylammonium iodide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19900730821

upstream raw materials:

2,6-dimethylphenyl propionate Li-enolate

2,6-dimethylphenyl (2R,3R,4S,5S,6S)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-oxoheptanoate

2,6-dimethylphenyl propionate

methyl 3,5-dihydoxy-2,4-dimethylpentanoate

Downstream raw materials:

bis(2,6-dimethylphenyl) (2S,3S,4R,5R,6S,7R,8R)-3,5,7-trihydroxy-2,4,6,8-tetramethyl-nonane-1,9-dioate

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