(3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one

Base Information

• Chemical Name: (3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one
• CAS No.: 828915-95-3
• Molecular Formula: C₅₅H₅₈O₅Si
• Molecular Weight: 827.148

Synonyms:(3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one

Chemical Property of (3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one

Chemical Property:

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Technology Process of (3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one

There total 10 articles about (3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one 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: 96.0%

chloro-trimethyl-silane (75-77-4) + (3aS,4S,7aR)-4-Hydroxy-5-((S)-1-methyl-4-trityloxy-butyl)-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one (828915-94-2) → (3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one (828915-95-3)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.200460936

Reference yield:

trityl chloride (76-83-5) → (3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one (828915-95-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 40 h / 20 °C

2.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3.5 h / 20 °C

3.1: 96 percent / TBAF; HOAc / tetrahydrofuran / 26 h / 20 °C

4.1: 90 percent / Red-Al / CH₂Cl₂; toluene / -20 - 20 °C

5.1: TBAF; 4 Angstroem molecular sieves / tetrahydrofuran / 4 h / Heating

5.2: 99 percent / KF; NaHCO₃; H₂O₂ / H₂O; tetrahydrofuran; methanol / 1 h / Heating

6.1: 75 percent / TEMPO; bis(acetoxy)iodobenzene / CH₂Cl₂ / 20 °C

7.1: 96 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; tetrabutyl ammonium fluoride; Dess-Martin periodane; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene; 2.1: Dess-Martin oxidation / 5.2: modified Tamao-Fleming oxidation;

DOI:10.1002/ejoc.200500739

Reference yield:

(1R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(dimethyl-phenyl-silanyl)-ethyl]-3-hydroxymethyl-2-((S)-4-hydroxy-1-methyl-butyl)-cyclohex-2-enol (828915-88-4) → (3aR,4S,7aR)-5-((S)-1-Methyl-4-trityloxy-butyl)-4-trimethylsilanyloxy-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one (828915-95-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 40 h / 20 °C

2.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3.5 h / 20 °C

3.1: 96 percent / TBAF; HOAc / tetrahydrofuran / 26 h / 20 °C

4.1: 90 percent / Red-Al / CH₂Cl₂; toluene / -20 - 20 °C

5.1: TBAF; 4 Angstroem molecular sieves / tetrahydrofuran / 4 h / Heating

5.2: 99 percent / KF; NaHCO₃; H₂O₂ / H₂O; tetrahydrofuran; methanol / 1 h / Heating

6.1: 75 percent / TEMPO; bis(acetoxy)iodobenzene / CH₂Cl₂ / 20 °C

7.1: 96 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; tetrabutyl ammonium fluoride; Dess-Martin periodane; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene; 2.1: Dess-Martin oxidation / 5.2: modified Tamao-Fleming oxidation;

DOI:10.1002/ejoc.200500739

upstream raw materials:

chloro-trimethyl-silane

(3aS,4S,7aR)-4-Hydroxy-5-((S)-1-methyl-4-trityloxy-butyl)-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one

trityl chloride

Formic acid (5S,8R,9S,9aR)-8-(tert-butyl-dimethyl-silanyloxy)-9-[2-(dimethyl-phenyl-silanyl)-ethyl]-5-methyl-2-oxo-2,3,4,5,7,8,9,9a-octahydro-benzo[b]oxepin-6-ylmethyl ester

Downstream raw materials:

(Z)-2-Methyl-but-2-enoic acid (3aR,4S,7aR)-3-methylene-5-((S)-1-methyl-4-trityloxy-butyl)-2-oxo-6-trityloxymethyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-yl ester

2-Methyl-acrylic acid (3aR,4S,7aR)-3-methylene-5-((S)-1-methyl-4-trityloxy-butyl)-2-oxo-6-trityloxymethyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-yl ester

(3aS,4S,7aR)-4-Hydroxy-3-methylene-5-((S)-1-methyl-4-trityloxy-butyl)-6-trityloxymethyl-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one

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