tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane

Base Information

• Chemical Name: tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane
• CAS No.: 890528-69-5
• Molecular Formula: C₅₅H₇₆O₅Si
• Molecular Weight: 845.291

Synonyms:

Chemical Property of tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane

There total 11 articles about tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane 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:

(E)-(R)-4-[(3R,5R,7R,8R,9S,10S,13R,17R)-7-Acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pent-2-enoic acid methyl ester (890528-66-2) → tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane (890528-69-5)

Guidance literature:

Multi-step reaction with 7 steps

1: OsO₄; K₃Fe(CN)6 / H₂O; 2-methyl-propan-2-ol / 20 h / 20 °C

2: 96 percent / PTSA / CH₂Cl₂ / 0 - 20 °C

3: 84 percent / aq. NaOH / methanol / 1 h / 0 °C

4: 95 percent / NaH / dimethylformamide / 0 - 20 °C

5: 36 h / -78 - 0 °C

6: Dess-Martin agent; aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

7: 82 percent / TiCl; Zn / CH₂Cl₂ / 25 °C

With sodium hydroxide; osmium(VIII) oxide; thallium chloride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); zinc; In methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2006.03.072

Reference yield:

(R)-4-[(3R,5R,7R,8R,9S,10S,13R,17R)-7-Acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-12-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester (890528-65-1) → tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane (890528-69-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: DBU; CS₂; CH₃I / dimethylformamide / 0 - 20 °C

1.2: 86 percent / Bu₃SnH; AIBN / toluene / 120 °C

2.1: LDA; PhSeBr / tetrahydrofuran / 4 h / -78 °C

2.2: 86 percent / aq. H₂O₂ / methanol / 2 h / 20 °C

3.1: OsO₄; K₃Fe(CN)6 / H₂O; 2-methyl-propan-2-ol / 20 h / 20 °C

4.1: 96 percent / PTSA / CH₂Cl₂ / 0 - 20 °C

5.1: 84 percent / aq. NaOH / methanol / 1 h / 0 °C

6.1: 95 percent / NaH / dimethylformamide / 0 - 20 °C

7.1: 36 h / -78 - 0 °C

8.1: Dess-Martin agent; aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

9.1: 82 percent / TiCl; Zn / CH₂Cl₂ / 25 °C

With carbon disulfide; sodium hydroxide; osmium(VIII) oxide; thallium chloride; Phenylselenyl bromide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium hexacyanoferrate(III); zinc; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Barton deoxygenation;

DOI:10.1016/j.tetlet.2006.03.072

Reference yield:

(R)-4-[(3R,5R,7R,8R,9S,10S,13R,14S,17R)-7-Acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-12-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester (890528-64-0) → tert-butyl-[17-{1-[5-(1-isopropyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-7-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane (890528-69-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dioxane / Photolysis

2.1: BF₃*OEt₂ / benzene / 25 °C

3.1: DBU; CS₂; CH₃I / dimethylformamide / 0 - 20 °C

3.2: 86 percent / Bu₃SnH; AIBN / toluene / 120 °C

4.1: LDA; PhSeBr / tetrahydrofuran / 4 h / -78 °C

4.2: 86 percent / aq. H₂O₂ / methanol / 2 h / 20 °C

5.1: OsO₄; K₃Fe(CN)6 / H₂O; 2-methyl-propan-2-ol / 20 h / 20 °C

6.1: 96 percent / PTSA / CH₂Cl₂ / 0 - 20 °C

7.1: 84 percent / aq. NaOH / methanol / 1 h / 0 °C

8.1: 95 percent / NaH / dimethylformamide / 0 - 20 °C

9.1: 36 h / -78 - 0 °C

10.1: Dess-Martin agent; aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

11.1: 82 percent / TiCl; Zn / CH₂Cl₂ / 25 °C

With carbon disulfide; sodium hydroxide; osmium(VIII) oxide; thallium chloride; Phenylselenyl bromide; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium hexacyanoferrate(III); zinc; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 3.1: Barton deoxygenation;

DOI:10.1016/j.tetlet.2006.03.072

upstream raw materials:

(E)-(R)-4-[(3R,5R,7R,8R,9S,10S,13R,17R)-7-Acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pent-2-enoic acid methyl ester

(R)-4-[(3R,5R,7R,8R,9S,10S,13R,14S,17R)-7-Acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-12-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

(R)-4-[(3R,5R,7R,8R,9S,10S,13R,17R)-7-Acetoxy-3-(tert-butyl-diphenyl-silanyloxy)-12-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

5-{1-[3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethyl}-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

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