2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate

Base Information

• Chemical Name: 2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate
• CAS No.: 106681-45-2
• Molecular Formula: C₁₆H₂₄O₅S
• Molecular Weight: 328.43
• Mol file: 106681-45-2.mol

Synonyms:

Chemical Property of 2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate

There total 5 articles about 2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate 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: 95.0%

4-methyl-3,4-O-isopropylidenepentane-1,3,4-triol (106681-21-4) + p-toluenesulfonyl chloride (98-59-9) → 2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate (106681-45-2)

Guidance literature:

With pyridine; 1.) 0 deg C, 2 h, 2.) -20 deg C, overnight;

DOI:10.1021/jo00381a021

Reference yield:

4-methylpent-3-en-1-ol (763-89-3) → 2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate (106681-45-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 25 deg C, 30 min, 2.) THF, 25 deg C, 5 h

2: 77 percent / N-methylmorpholine N-oxide hydrate, osmium tetra-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

3: 97 percent / conc. H₂SO₄, Na₂SO₄ / Ambient temperature

4: 98 percent / H₂ / 10percent Pd/C / ethanol / 24 h / 3361.5 Torr

5: 95 percent / pyridine / 1.) 0 deg C, 2 h, 2.) -20 deg C, overnight

With pyridine; osmium(VIII) oxide; sulfuric acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; sodium sulfate; palladium on activated charcoal; In ethanol; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo00381a021

Reference yield:

(((4-methylpent-3-en-1-yl)oxy)methyl)benzene (106681-18-9) → 2-methyl-2,3-O-isopropylidenepentane-2,3,5-triol 5-p-toluenesulfonate (106681-45-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / N-methylmorpholine N-oxide hydrate, osmium tetra-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

2: 97 percent / conc. H₂SO₄, Na₂SO₄ / Ambient temperature

3: 98 percent / H₂ / 10percent Pd/C / ethanol / 24 h / 3361.5 Torr

4: 95 percent / pyridine / 1.) 0 deg C, 2 h, 2.) -20 deg C, overnight

With pyridine; osmium(VIII) oxide; sulfuric acid; hydrogen; 4-methylmorpholine N-oxide; sodium sulfate; palladium on activated charcoal; In ethanol; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo00381a021

upstream raw materials:

4-methyl-3,4-O-isopropylidenepentane-1,3,4-triol

p-toluenesulfonyl chloride

4-methylpent-3-en-1-ol

(((4-methylpent-3-en-1-yl)oxy)methyl)benzene

Downstream raw materials:

2-methyl-5-N-pyrrolylpentane-2,3-diol 3-p-toluenesulfonate