Propanoic acid, 2,2-dimethyl-, (1R,2E)-1-[(4S,5S)-5-[1-hydroxy-3-[(4-methylphenyl)sulfonyl]-2-propynyl] -2,2-dimethyl-1,3-dioxolan-4-yl]-2,4-pentadienyl ester

Base Information

Chemical Name:Propanoic acid, 2,2-dimethyl-, (1R,2E)-1-[(4S,5S)-5-[1-hydroxy-3-[(4-methylphenyl)sulfonyl]-2-propynyl] -2,2-dimethyl-1,3-dioxolan-4-yl]-2,4-pentadienyl ester
CAS No.:596092-44-3
Molecular Formula:C25H32O7S
Molecular Weight:476.591
Hs Code.:

Propanoic acid, 2,2-dimethyl-,
(1R,2E)-1-[(4S,5S)-5-[1-hydroxy-3-[(4-methylphenyl)sulfonyl]-2-propynyl]
-2,2-dimethyl-1,3-dioxolan-4-yl]-2,4-pentadienyl ester

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Chemical Property of Propanoic acid, 2,2-dimethyl-, (1R,2E)-1-[(4S,5S)-5-[1-hydroxy-3-[(4-methylphenyl)sulfonyl]-2-propynyl] -2,2-dimethyl-1,3-dioxolan-4-yl]-2,4-pentadienyl ester

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Technology Process of Propanoic acid, 2,2-dimethyl-, (1R,2E)-1-[(4S,5S)-5-[1-hydroxy-3-[(4-methylphenyl)sulfonyl]-2-propynyl] -2,2-dimethyl-1,3-dioxolan-4-yl]-2,4-pentadienyl ester

There total 6 articles about Propanoic acid, 2,2-dimethyl-, (1R,2E)-1-[(4S,5S)-5-[1-hydroxy-3-[(4-methylphenyl)sulfonyl]-2-propynyl] -2,2-dimethyl-1,3-dioxolan-4-yl]-2,4-pentadienyl 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:

: 34452-56-7
trimethylsilyl p-tolylsulfonylacetylene

: 596092-46-5
2,2-Dimethyl-propionic acid (E)-(R)-1-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-penta-2,4-dienyl ester

: 596092-44-3
2,2-Dimethyl-propionic acid (E)-(R)-1-{(4S,5S)-5-[1-hydroxy-3-(toluene-4-sulfonyl)-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-penta-2,4-dienyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/ol034823f

Reference yield:

: 136032-73-0,127251-09-6
4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol

: 596092-44-3
2,2-Dimethyl-propionic acid (E)-(R)-1-{(4S,5S)-5-[1-hydroxy-3-(toluene-4-sulfonyl)-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-penta-2,4-dienyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 0.58 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -78 °C

2.2: 22 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 2 h / -78 °C

3.1: pyridine; DMAP / CH₂Cl₂ / 12 h / Heating

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.58 h / -78 °C

6.1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / -78 °C

With pyridine; dmap; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane;
DOI:10.1021/ol034823f

Reference yield:

: 101331-92-4
4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose

: 596092-44-3
2,2-Dimethyl-propionic acid (E)-(R)-1-{(4S,5S)-5-[1-hydroxy-3-(toluene-4-sulfonyl)-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-penta-2,4-dienyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -78 °C

1.2: 22 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 2 h / -78 °C

2.1: pyridine; DMAP / CH₂Cl₂ / 12 h / Heating

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.58 h / -78 °C

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / -78 °C

With pyridine; dmap; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane;
DOI:10.1021/ol034823f