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

Base Information

• Chemical Name: toluene-4-sulfonic acid (2'R,3'S)-3'-pent-4-enyloxytetrahydropyran-2'-ylmethyl ester
• CAS No.: 234111-47-8
• Molecular Formula: C₁₈H₂₆O₅S
• Molecular Weight: 354.467

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

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

Chemical Property:

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

There total 2 articles about toluene-4-sulfonic acid (2'R,3'S)-3'-pent-4-enyloxytetrahydropyran-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: 78.0%

toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester (161946-35-6) + bromopentene (1119-51-3) → toluene-4-sulfonic acid (2'R,3'S)-3'-pent-4-enyloxytetrahydropyran-2'-ylmethyl ester (234111-47-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; at 0 - 25 ℃; for 6h;

DOI:10.1021/jo9901438

Reference yield:

(2R,3S)-2-hydroxymethyltetrahydropyran-3-ol (51450-45-4) → toluene-4-sulfonic acid (2'R,3'S)-3'-pent-4-enyloxytetrahydropyran-2'-ylmethyl ester (234111-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / NEt₃, DMAP / CH₂Cl₂ / 0 - 25 °C

2: 78 percent / KH, n-Bu₄NI / tetrahydrofuran / 6 h / 0 - 25 °C

With dmap; tetra-(n-butyl)ammonium iodide; potassium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo9901438

Reference yield: 98.0%

potassium cyanide (151-50-8) + toluene-4-sulfonic acid (2'R,3'S)-3'-pent-4-enyloxytetrahydropyran-2'-ylmethyl ester (234111-47-8) → (2'R,3'S)-(3'-pent-4-enyloxytetrahydropyran-2'-yl)acetonitrile (234111-50-3)

Guidance literature:

In dimethyl sulfoxide; at 50 ℃; for 6h;

DOI:10.1021/jo9901438

upstream raw materials:

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

bromopentene

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

Downstream raw materials:

(2'R,3'S)-(3'-pent-4-enyloxytetrahydropyran-2'-yl)acetonitrile

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