Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

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Chemical Name:Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester
CAS No.:89927-22-0
Molecular Formula:C₁₉H₂₄O₆S
Molecular Weight:380.462
Hs Code.:

Synonyms:Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

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Chemical Property of Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

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Technology Process of Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

There total 15 articles about Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl 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: 90.0%

: 89927-21-9
Acetic acid (S)-1-[(S)-6-hydroxy-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

: 89927-22-0
Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: With jones reagent; In acetone; at 0 ℃; for 3h;
DOI:10.1016/S0040-4039(01)91157-8

Reference yield:

: 88948-50-9
{(4S,5S)-5-Hydroxymethyl-2-[2-(toluene-4-sulfonyl)-ethyl]-[1,3]dioxolan-4-yl}-methanol

: 89927-22-0
Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: sulfonation

2: intramolecular alkylation

3: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

4: 95 percent / K₂CO₃ / methanol / 0.5 h / 0 °C

5: 1.)(n-Pr)2CuLi / 2.)acetylation

6: Br₂ / CH₂Cl₂ / 0.08 h / 0 °C

7: 5percent aq.K₂CO₃ / tetrahydrofuran / 0.25 h / 0 °C

8: NaOMe / tetrahydrofuran / 0.5 h / 0 °C

9: 90 percent / Jones reagent / acetone / 3 h / 0 °C

With jones reagent; boron trifluoride diethyl etherate; bromine; sodium methylate; potassium carbonate; di-n-propylcopperlithium; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1016/S0040-4039(01)91157-8

Reference yield:

: 88948-49-6
(4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

: 89927-22-0
Acetic acid (S)-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: reduction

2: sulfonation

3: intramolecular alkylation

4: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 0 °C

5: 95 percent / K₂CO₃ / methanol / 0.5 h / 0 °C

6: 1.)(n-Pr)2CuLi / 2.)acetylation

7: Br₂ / CH₂Cl₂ / 0.08 h / 0 °C

8: 5percent aq.K₂CO₃ / tetrahydrofuran / 0.25 h / 0 °C

9: NaOMe / tetrahydrofuran / 0.5 h / 0 °C

10: 90 percent / Jones reagent / acetone / 3 h / 0 °C

With jones reagent; boron trifluoride diethyl etherate; bromine; sodium methylate; potassium carbonate; di-n-propylcopperlithium; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1016/S0040-4039(01)91157-8