Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester
CAS No.:204325-80-4
Molecular Formula:C₂₂H₂₈O₆S
Molecular Weight:420.527
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

There total 12 articles about Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl 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: 65.0%

: 204325-79-1
((R)-Toluene-4-sulfinyl)-acetic acid (S)-2-benzyloxy-6-oxo-2-(toluene-4-sulfonyloxymethyl)-heptyl ester

: 204325-80-4
Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

Guidance literature:: With potassium hydroxide; In isopropyl alcohol; for 0.166667h; Ambient temperature;
DOI:10.1248/cpb.46.217

Reference yield:

: 204325-69-9
1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexen-2-ol

: 204325-80-4
Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) NaH, tetra-n-butylammonium iodide / 1.) DMF, RT, 10 min, 2.) DMF, RT, 5 h

2: 1.) OsO₄, 2.) NaIO₄ / 1.) ether, water, RT, 5 min, 2.) ether, water, RT, 3 h

3: 1.) LDA / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min

4: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / Ambient temperature

5: 90 percent / p-TsOH*H₂O / methanol / 3 h / Ambient temperature

6: 75 percent / ZnCl₂ / CH₂Cl₂ / 10 h / Ambient temperature

7: 52 percent / 2,6-lutidine, TiCl₄ / tetrahydrofuran / a) from -78 deg C to 5 deg C, 5 h, b) 5 deg C, 15 h

8: 87 percent / DMAP / CH₂Cl₂ / 13.5 h / Ambient temperature

9: 63 percent / O₃ / CH₂Cl₂ / 0.02 h / -78 °C

10: 43 percent / tetrahydrofuran / 18.5 h / Heating

11: 100 percent / H₂ / 10percent Pd/C / methanol / 760 Torr

12: 65 percent / 1 N KOH / propan-2-ol / 0.17 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium periodate; osmium(VIII) oxide; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol;
DOI:10.1248/cpb.46.217

Reference yield:

: 204325-70-2
2-benzyloxy-1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexene

: 204325-80-4
Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) OsO₄, 2.) NaIO₄ / 1.) ether, water, RT, 5 min, 2.) ether, water, RT, 3 h

2: 1.) LDA / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min

3: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / Ambient temperature

4: 90 percent / p-TsOH*H₂O / methanol / 3 h / Ambient temperature

5: 75 percent / ZnCl₂ / CH₂Cl₂ / 10 h / Ambient temperature

6: 52 percent / 2,6-lutidine, TiCl₄ / tetrahydrofuran / a) from -78 deg C to 5 deg C, 5 h, b) 5 deg C, 15 h

7: 87 percent / DMAP / CH₂Cl₂ / 13.5 h / Ambient temperature

8: 63 percent / O₃ / CH₂Cl₂ / 0.02 h / -78 °C

9: 43 percent / tetrahydrofuran / 18.5 h / Heating

10: 100 percent / H₂ / 10percent Pd/C / methanol / 760 Torr

11: 65 percent / 1 N KOH / propan-2-ol / 0.17 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium periodate; osmium(VIII) oxide; hydrogen; titanium tetrachloride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol;
DOI:10.1248/cpb.46.217