(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

Base Information

Chemical Name:(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate
CAS No.:1374633-04-1
Molecular Formula:C₂₈H₃₂O₈S
Molecular Weight:528.623
Hs Code.:

Synonyms:(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

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Chemical Property of (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

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Technology Process of (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

There total 6 articles about (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate 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: 95.0%

: 1374633-03-0
(2S,3R,4R,5S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-(p-tolylthio)tetrahydrofuran-3-yl 4-oxopentanoate

: 98-88-4
benzoyl chloride

: 1374633-04-1
(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

Guidance literature:: With pyridine; at 0 - 20 ℃; for 2h;
DOI:10.1016/j.tet.2014.04.069

Reference yield:

: 920267-56-7
4-methylphenyl 1-thio-β-D-galactofuranoside

: 1374633-04-1
(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1: sulfuric acid; copper(II) sulfate / 24 h / 20 °C / Inert atmosphere

2: 1H-imidazole; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

3: dmap; dicyclohexyl-carbodiimide / 3 h / 20 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

5: pyridine / 5 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; sulfuric acid; tetrabutyl ammonium fluoride; copper(II) sulfate; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2012.03.074

Reference yield:

: 1374633-02-9
(2S,3S,4R,5S)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(p-tolylthio)tetrahydrofuran-3-yl 4-oxopentanoate

: 1374633-04-1
(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

2: pyridine / 5 h / 0 - 20 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/j.tet.2012.03.074