Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester

Base Information

• Chemical Name: Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester
• CAS No.: 182822-17-9
• Molecular Formula: C₄₆H₆₆O₆Si₂
• Molecular Weight: 771.197

Synonyms:Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester

Chemical Property of Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester

Chemical Property:

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Technology Process of Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester

There total 5 articles about Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester 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: 86.0%

benzoic acid (65-85-0,8013-63-6) + 4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-(hydroxy-phenyl-methyl)-5H-furan-2-one (182822-15-7) → Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester (182822-17-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1016/0040-4020(96)00753-3

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester (182822-17-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

2: 90 percent / pyridine / 3.5 h / 20 °C

3: 1.) NaH, N-methylpyrrolidone / 1.) -20 deg C, 30 min, 2.) N-methylpyrrolidone, -20 deg C, 40 min

4: 86 percent / DMAP, DCC / CH₂Cl₂ / 8 h / 20 °C

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; sodium hydride; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/0040-4020(96)00753-3

Reference yield:

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one (182573-64-4) → Benzoic acid {3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-oxo-2,5-dihydro-furan-2-yl}-phenyl-methyl ester (182822-17-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / pyridine / 3.5 h / 20 °C

2: 1.) NaH, N-methylpyrrolidone / 1.) -20 deg C, 30 min, 2.) N-methylpyrrolidone, -20 deg C, 40 min

3: 86 percent / DMAP, DCC / CH₂Cl₂ / 8 h / 20 °C

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; sodium hydride; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/0040-4020(96)00753-3

upstream raw materials:

benzoic acid

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5-(hydroxy-phenyl-methyl)-5H-furan-2-one

t-butyldimethylsiyl triflate

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one

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