(2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

Base Information

Chemical Name:(2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate
CAS No.:1446347-66-5
Molecular Formula:C₂₂H₃₄O₈
Molecular Weight:426.507
Hs Code.:

Synonyms:(2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

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Chemical Property of (2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

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Technology Process of (2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

There total 20 articles about (2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate 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: 78.0%

: (2R,3R,4S,7S)-methyl 7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethyl-3-(2-((4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl)acetoxy)heptanoate

: 1446347-66-5
(2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 0 - 20 ℃; for 4h; Inert atmosphere;
DOI:10.1039/c3ob40252e

Reference yield:

: 96013-95-5
3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde

: 1446347-66-5
(2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 12 steps

1: tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2: lipase Amino-I / di-isopropyl ether / 48 h / 20 °C / Inert atmosphere

3: sodium hydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / Inert atmosphere; Reflux

5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

8: sodium chlorite; sodium dihydrogenphosphate; water / tert-butyl alcohol / 12 h / 0 - 20 °C / Inert atmosphere

9: diethyl ether / 0.5 h / 0 °C / Inert atmosphere

10: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

11: triethylamine; 2,4,6-trichlorobenzoyl chloride; dmap / toluene / 10 h / Inert atmosphere

12: toluene-4-sulfonic acid / methanol / 4 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium chlorite; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; lipase Amino-I; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; di-isopropyl ether; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1039/c3ob40252e

Reference yield:

: 1-(3-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol

: 1446347-66-5
(2R,3R,4S,7S)-methyl 3-((3R,4R)-3,4-dihydroxy pentanoyloxy)-7-(3-hydroxyphenyl)-7-methoxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 11 steps

1: lipase Amino-I / di-isopropyl ether / 48 h / 20 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / Inert atmosphere; Reflux

4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

7: sodium chlorite; sodium dihydrogenphosphate; water / tert-butyl alcohol / 12 h / 0 - 20 °C / Inert atmosphere

8: diethyl ether / 0.5 h / 0 °C / Inert atmosphere

9: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

10: triethylamine; 2,4,6-trichlorobenzoyl chloride; dmap / toluene / 10 h / Inert atmosphere

11: toluene-4-sulfonic acid / methanol / 4 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium chlorite; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; lipase Amino-I; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; di-isopropyl ether; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1039/c3ob40252e