[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

Base Information

Chemical Name:[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid
CAS No.:172268-48-3
Molecular Formula:C₄₄H₆₈O₈Si
Molecular Weight:753.105
Hs Code.:

[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

Synonyms:[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

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Chemical Property of [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

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Technology Process of [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

There total 33 articles about [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid 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: 95.0%

: 172268-73-4
[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

: 172268-48-3
[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol;
DOI:10.1021/ja00153a031

Reference yield:

: 172587-76-7
(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

: 172268-48-3
[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

Guidance literature:: Multi-step reaction with 19 steps

1: 96 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

2: 83 percent / dicyclohexylcarbodiimide, dimethyl sulfoxide, trifluoroacetic acid, pyridine / benzene / 2 h / Ambient temperature

3: 80 percent / magnesium chloride / tetrahydrofuran; diethyl ether / 1.) reflux 20 min, 2.) -78 deg C, 1.5 h

4: 95 percent / H₂, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h

5: 1.) potassium hydride, 18-crown-6, 2.) n-butyllithium / 1.) THF, room temperature, 45 min, 2.) THF, hexane, -78 deg C, 1.5 h

6: 74 percent / p-toluenesulfonic acid / dimethylformamide; H₂O / 24 h / Heating

7: 90 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.67 h / 0 °C

8: 96 percent / silver carbonate on Celite / benzene / 19 h / Heating

9: 87 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

10: 94 percent / citric acid / 1.5 h / Heating

11: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.67 h / Ambient temperature

12: 62 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

13: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

14: 88 percent / triethylsilane / 10percent Pd on carbon / CH₂Cl₂ / 2 h / Ambient temperature

15: 82 percent / magnesium bromide / tetrahydrofuran; diethyl ether; benzene; pentane / 1 h / -78 °C

16: 94 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / Ambient temperature

17: 97 percent / 10-camphorsulfonic acid / methanol / 0 - 4 °C

18: 90 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 1.) -25 deg C, 17 h, 2.) 0 deg C, 2 h

19: 95 percent / LiOH / tetrahydrofuran; methanol; H₂O / Ambient temperature

With pyridine; 2,6-dimethylpyridine; quinoline; triethylsilane; dmap; lithium hydroxide; n-butyllithium; 18-crown-6 ether; (1S)-10-camphorsulfonic acid; hydrogen; potassium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; silver carbonate; trifluoroacetic acid; citric acid; magnesium bromide; magnesium chloride; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; pentane; benzene;
DOI:10.1021/ja972497r

Reference yield:

: 1-[(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

: 172268-48-3
[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid

Guidance literature:: Multi-step reaction with 18 steps

1: 83 percent / dicyclohexylcarbodiimide, dimethyl sulfoxide, trifluoroacetic acid, pyridine / benzene / 2 h / Ambient temperature

2: 80 percent / magnesium chloride / tetrahydrofuran; diethyl ether / 1.) reflux 20 min, 2.) -78 deg C, 1.5 h

3: 95 percent / H₂, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h

4: 1.) potassium hydride, 18-crown-6, 2.) n-butyllithium / 1.) THF, room temperature, 45 min, 2.) THF, hexane, -78 deg C, 1.5 h

5: 74 percent / p-toluenesulfonic acid / dimethylformamide; H₂O / 24 h / Heating

6: 90 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.67 h / 0 °C

7: 96 percent / silver carbonate on Celite / benzene / 19 h / Heating

8: 87 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

9: 94 percent / citric acid / 1.5 h / Heating

10: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.67 h / Ambient temperature

11: 62 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C

12: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

13: 88 percent / triethylsilane / 10percent Pd on carbon / CH₂Cl₂ / 2 h / Ambient temperature

14: 82 percent / magnesium bromide / tetrahydrofuran; diethyl ether; benzene; pentane / 1 h / -78 °C

15: 94 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / Ambient temperature

16: 97 percent / 10-camphorsulfonic acid / methanol / 0 - 4 °C

17: 90 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 1.) -25 deg C, 17 h, 2.) 0 deg C, 2 h

18: 95 percent / LiOH / tetrahydrofuran; methanol; H₂O / Ambient temperature

With pyridine; 2,6-dimethylpyridine; quinoline; triethylsilane; dmap; lithium hydroxide; n-butyllithium; 18-crown-6 ether; (1S)-10-camphorsulfonic acid; hydrogen; potassium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; silver carbonate; trifluoroacetic acid; citric acid; magnesium bromide; magnesium chloride; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; pentane; benzene;
DOI:10.1021/ja972497r