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

Base Information

Chemical Name: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
CAS No.:828915-97-5
Molecular Formula:C₅₇H₅₄O₆
Molecular Weight:835.052
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 13 articles about 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 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: 85.0%

: 760-93-0
methacryloyl anhydride

: 828915-96-4
(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

: 828915-97-5
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

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/anie.200460936

Reference yield:

: 76-83-5
trityl chloride

: 828915-97-5
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

Guidance literature:: Multi-step reaction with 9 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

8.1: NaH / tetrahydrofuran / 100 °C

8.2: 61 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

9.1: 85 percent / Et₃N; DMAP / tetrahydrofuran / 3 h / 0 - 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; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; 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:

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

: 828915-97-5
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

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 100 °C

1.2: 61 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

2.1: 85 percent / Et₃N; DMAP / tetrahydrofuran / 3 h / 0 - 20 °C

With dmap; sodium hydride; triethylamine; In tetrahydrofuran;
DOI:10.1002/ejoc.200500739