(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

Base Information

Chemical Name:(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
CAS No.:828915-98-6
Molecular Formula:C₅₈H₅₆O₆
Molecular Weight:849.079
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 15 articles about (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 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: 60.0%

: 565-63-9
Angelic acid

: 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

: 828915-98-6
(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

Guidance literature:: Angelic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 20 ℃; for 3.5h;

(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; In toluene; at 100 ℃; for 8h;
DOI:10.1002/ejoc.200500739

Reference yield:

: 76-83-5
trityl chloride

: 828915-98-6
(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

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: 2,4,6-trichlorobenzoyl chloride; Et₃N / toluene / 3.5 h / 20 °C

9.2: 60 percent / toluene / 8 h / 100 °C

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; 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:

: 828915-88-4
(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

: 828915-98-6
(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

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: 2,4,6-trichlorobenzoyl chloride; Et₃N / toluene / 3.5 h / 20 °C

9.2: 60 percent / toluene / 8 h / 100 °C

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; 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