Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-pentyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-pentyl ester
• CAS No.: 443283-57-6
• Molecular Formula: C₁₅H₂₂O₄S
• Molecular Weight: 298.403
• Mol file: 443283-57-6.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-pentyl ester

There total 1 articles about Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-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:

[3R,4S,4'S]-4-[acyl(4'-isopropyl-2'-oxazolidone)]-2-methylhex-5-en-3-ol (108735-30-4) → Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-pentyl ester (443283-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tributylborane; acetic acid / tetrahydrofuran / 1.5 h / 23 °C

1.2: lithium borohydride / tetrahydrofuran / 1 h / 0 °C

1.3: 85 percent / H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C / pH 7

2.1: 81 percent / pyridine / 4 h / 23 °C

With pyridine; tributyl borane; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo016413f

Reference yield:

Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-pentyl ester (443283-57-6) → (2S,3S,4S,5R)-3-Hydroxy-2-methoxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-heptanal

Guidance literature:

Multi-step reaction with 7 steps

1.1: 66 percent / lithium aluminum hydride / diethyl ether / -25 °C

2.1: sodium hydride / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 23 °C

2.2: 86 percent / tetrahydrofuran; dimethylsulfoxide / 23 °C

3.1: N-methylmorpholine N-oxide / osmium tetroxide / acetone; tetrahydrofuran; H₂O / 3 h / 23 °C / pH 7.0

4.1: aq. NaIO₄ / tetrahydrofuran; H₂O / 23 °C / pH 7.0

5.1: 60 mg / chromium(II) chloride; trimethylsilyl iodide / 4.5 h / -42 °C

6.1: N-methylmorpholine N-oxide / osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol

7.1: NaIO₄ / tetrahydrofuran; H₂O / 0.75 h / 20 °C

With chromium dichloride; sodium periodate; lithium aluminium tetrahydride; trimethylsilyl iodide; sodium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; 5.1: Takai reaction;

DOI:10.1021/jo016413f

Reference yield:

Toluene-4-sulfonic acid (2R,3R)-3-hydroxy-4-methyl-2-vinyl-pentyl ester (443283-57-6) → (2R,3S,4S,5R)-2-Methoxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-heptane-1,3-diol

Guidance literature:

Multi-step reaction with 8 steps

1.1: 66 percent / lithium aluminum hydride / diethyl ether / -25 °C

2.1: sodium hydride / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 23 °C

2.2: 86 percent / tetrahydrofuran; dimethylsulfoxide / 23 °C

3.1: N-methylmorpholine N-oxide / osmium tetroxide / acetone; tetrahydrofuran; H₂O / 3 h / 23 °C / pH 7.0

4.1: aq. NaIO₄ / tetrahydrofuran; H₂O / 23 °C / pH 7.0

5.1: 60 mg / chromium(II) chloride; trimethylsilyl iodide / 4.5 h / -42 °C

6.1: N-methylmorpholine N-oxide / osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol

7.1: NaIO₄ / tetrahydrofuran; H₂O / 0.75 h / 20 °C

8.1: NaBH₄ / methanol / 1 h

With chromium dichloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; trimethylsilyl iodide; sodium hydride; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; 5.1: Takai reaction;

DOI:10.1021/jo016413f

upstream raw materials:

[3R,4S,4'S]-4-[acyl(4'-isopropyl-2'-oxazolidone)]-2-methylhex-5-en-3-ol

Downstream raw materials:

Acetic acid (1R,4S,5R,6R)-5-hydroxy-1-[(1S,2R)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-butyl]-4,6-dimethyl-3-oxo-oct-7-enyl ester

(3R,4R,5S,8R,9R,10R)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-10-(4-methoxy-benzyloxy)-3,5,9,11-tetramethyl-dodec-1-en-6-one

Acetic acid (1R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-1-[(1S,2R)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-butyl]-4,6-dimethyl-3-oxo-oct-7-enyl ester