2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate

Base Information

Chemical Name:2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate
CAS No.:132950-34-6
Molecular Formula:C₃₇H₅₀O₅Si
Molecular Weight:602.886
Hs Code.:

Synonyms:2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate

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Chemical Property of 2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate

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Technology Process of 2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate

There total 18 articles about 2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate 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: 97.0%

: 132950-33-5
2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-dihydroxy-2,4,6-trimethylheptanoate

: 77-76-9
2,2-dimethoxy-propane

: 132950-34-6
2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate

Guidance literature:: With camphor-10-sulfonic acid; for 5h;
DOI:10.1002/hlca.19900730821

Reference yield:

: 105365-06-8
methyl 3,5-dihydoxy-2,4-dimethylpentanoate

: 132950-34-6
2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate

Guidance literature:: Multi-step reaction with 15 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

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:

: 89329-05-5
1-methyl hydrogen (3S,2R,4S)-3-hydroxy-2,4-dimethylglutarate

: 132950-34-6
2,6-dimethylphenyl (2R,3R,4S,5S,6S)-7-<(tert-butyl)diphenylsilyloxy>-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanoate

Guidance literature:: Multi-step reaction with 16 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

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