toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

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Chemical Name:toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester
CAS No.:944249-90-5
Molecular Formula:C₂₃H₂₀O₅S
Molecular Weight:408.475
Hs Code.:

Synonyms:toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

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Chemical Property of toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

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Technology Process of toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

There total 8 articles about toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl 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: 69.0%

: 944249-89-2
toluene-4-sulfonic acid 4-[(R)-1-(4-formyl-2-iodophenoxy)allyl]phenyl ester

: 944249-90-5
toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 2h;
DOI:10.1039/b704211f

Reference yield:

: 944249-84-7
(2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester

: 944249-90-5
toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C

2: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -25 °C

3: 64 percent / aq. NaOH / 2.5 h / 70 °C

4: 100 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

5: 71 percent / NaI / butan-2-one / 4 h / Heating

6: 69 percent / Bu₃SnH; AIBN / toluene / 2 h / 80 °C

With tert.-butylhydroperoxide; sodium hydroxide; (-)-diisopropyl tartrate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triethylamine; sodium iodide; titanium(IV) isopropylate; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; toluene; butanone; 2: Sharpless asymmetric epoxidation;
DOI:10.1039/b704211f

Reference yield:

: 944249-85-8
toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester

: 944249-90-5
toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -25 °C

2: 64 percent / aq. NaOH / 2.5 h / 70 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

4: 71 percent / NaI / butan-2-one / 4 h / Heating

5: 69 percent / Bu₃SnH; AIBN / toluene / 2 h / 80 °C

With tert.-butylhydroperoxide; sodium hydroxide; (-)-diisopropyl tartrate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; triethylamine; sodium iodide; titanium(IV) isopropylate; In 2,2,4-trimethylpentane; dichloromethane; toluene; butanone; 1: Sharpless asymmetric epoxidation;
DOI:10.1039/b704211f