toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester
• CAS No.: 176738-39-9
• Molecular Formula: C₁₆H₂₂O₅S
• Molecular Weight: 326.414
• Mol file: 176738-39-9.mol

Synonyms:toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester

Chemical Property of toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester

There total 6 articles about toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl 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: 93.0%

toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester (161946-35-6) + allyl bromide (106-95-6) → toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester (176738-39-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 10h;

DOI:10.1016/0040-4039(96)00408-X

Reference yield:

(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (125901-90-8) → toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester (176738-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / hydrogen / 10percent Pd/C / methanol / 8 h

2: 77 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h / 0 °C

3: 93 percent / NaH, nBu₄NI / dimethylformamide / 10 h / 0 °C

With dmap; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)00408-X

Reference yield:

((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (149342-25-6,92131-91-4) → toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester (176738-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / NaOMe / methanol / 0.5 h

2: 99 percent / hydrogen / 10percent Pd/C / methanol / 8 h

3: 77 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h / 0 °C

4: 93 percent / NaH, nBu₄NI / dimethylformamide / 10 h / 0 °C

With dmap; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)00408-X

upstream raw materials:

toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester

allyl bromide

(2R,3S)-2-hydroxymethyltetrahydropyran-3-ol

p-toluenesulfonyl chloride

Downstream raw materials:

Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

(2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile