Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester

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Chemical Name:Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester
CAS No.:83928-44-3
Molecular Formula:C₃₉H₆₃NO₉S
Molecular Weight:721.997
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester

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Chemical Property of Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester

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Technology Process of Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester

There total 9 articles about Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl 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:

: 54005-75-3
1-iodo-7,7-(1,3-dioxolane)heptane

: 83928-44-3
Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 45 percent / NaH / dimethylformamide / 4 h / 50 °C

2: 1.) KOH / 1.) MeOH, 3.) imidazole

3: 93 percent / Na(Hg), Na₂HPO₄ / ethanol / 12 h / Ambient temperature

4: 1.) i-Bu₂AlH, 2.) Me₂SO, (COCl)2, 3.) Et₃N / 1.) THF, -50 deg C

5: 1.) 18-crown-6, 2.) PhCH₂NMe₃F / 1.) 0 deg C, 2.) THF, H₂O, 0 deg C, 30 min

6: pyridinium p-toluenesulfonate / CH₂Cl₂

7: n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: Et₃N / CH₂Cl₂

With potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; trimethyl(benzyl)ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00339a043

Reference yield:

: 83918-42-7
(3S,4S)-4-[(E)-(R)-3-(Tetrahydro-pyran-2-yloxy)-oct-1-enyl]-3-(toluene-4-sulfonyl)-tetrahydro-pyran-2-one

: 83928-44-3
Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 45 percent / NaH / dimethylformamide / 4 h / 50 °C

2: 1.) KOH / 1.) MeOH, 3.) imidazole

3: 93 percent / Na(Hg), Na₂HPO₄ / ethanol / 12 h / Ambient temperature

4: 1.) i-Bu₂AlH, 2.) Me₂SO, (COCl)2, 3.) Et₃N / 1.) THF, -50 deg C

5: 1.) 18-crown-6, 2.) PhCH₂NMe₃F / 1.) 0 deg C, 2.) THF, H₂O, 0 deg C, 30 min

6: pyridinium p-toluenesulfonate / CH₂Cl₂

7: n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: Et₃N / CH₂Cl₂

With potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; trimethyl(benzyl)ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00339a043

Reference yield:

: 83928-40-9
(E)-(3R,6S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(6-[1,3]dioxolan-2-yl-hexyl)-6-(tetrahydro-pyran-2-yloxy)-undec-4-enal

: 83928-44-3
Toluene-4-sulfonic acid (E)-(3S,6R)-3-{1-[cyano-(1-ethoxy-ethoxy)-methyl]-7-[1,3]dioxolan-2-yl-heptyl}-6-(tetrahydro-pyran-2-yloxy)-undec-4-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) 18-crown-6, 2.) PhCH₂NMe₃F / 1.) 0 deg C, 2.) THF, H₂O, 0 deg C, 30 min

2: pyridinium p-toluenesulfonate / CH₂Cl₂

3: n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

4: Et₃N / CH₂Cl₂

With 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; trimethyl(benzyl)ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00339a043