Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester
• CAS No.: 122358-36-5
• Molecular Formula: C₂₀H₃₂O₅S
• Molecular Weight: 384.537
• Mol file: 122358-36-5.mol

Synonyms:Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester

Chemical Property of Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester

There total 8 articles about Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-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:

(2E)-2-methyl-2-penten-1-ol (16958-19-3) → Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester (122358-36-5)

Guidance literature:

Multi-step reaction with 7 steps

1: (+) diethyl tartrate, VO(acac)2, 70percent aq. tert-butylhydroperoxide / benzene

2: 1.) oxalyl chloride, dmso, 2.) Et₃N / CH₂Cl₂

3: 1.) NaH / THF

4: formic acid, Et₃N / Pd₂(dba)3CHCl₃, n-Bu₃P / dioxane / 1.5 h / Ambient temperature

5: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h / 0 °C

6: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

7: pyridine / 1 h / 0 °C

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; formic acid; oxalyl dichloride; bis(acetylacetonate)oxovanadium; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tributylphosphine; In 1,4-dioxane; diethyl ether; dichloromethane; benzene;

DOI:10.1021/ja00198a045

Reference yield:

((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol (76639-80-0) → Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester (122358-36-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) oxalyl chloride, dmso, 2.) Et₃N / CH₂Cl₂

2: 1.) NaH / THF

3: formic acid, Et₃N / Pd₂(dba)3CHCl₃, n-Bu₃P / dioxane / 1.5 h / Ambient temperature

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h / 0 °C

5: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

6: pyridine / 1 h / 0 °C

With pyridine; lithium aluminium tetrahydride; formic acid; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tributylphosphine; In 1,4-dioxane; diethyl ether; dichloromethane;

DOI:10.1021/ja00198a045

Reference yield:

(2R,3S)-3-ethyl-2-methyl-oxirane-2-carbaldehyde (131829-44-2) → Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester (122358-36-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / THF

2: formic acid, Et₃N / Pd₂(dba)3CHCl₃, n-Bu₃P / dioxane / 1.5 h / Ambient temperature

3: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h / 0 °C

4: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

5: pyridine / 1 h / 0 °C

With pyridine; lithium aluminium tetrahydride; formic acid; sodium hydride; toluene-4-sulfonic acid; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tributylphosphine; In 1,4-dioxane; diethyl ether; dichloromethane;

DOI:10.1021/ja00198a045

upstream raw materials:

(4S,5S)-4-Methyl-5-(tetrahydro-pyran-2-yloxy)-heptan-1-ol

p-toluenesulfonyl chloride

3,4-dihydro-2H-pyran

(2E)-2-methyl-2-penten-1-ol