3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose

Base Information

• Chemical Name: 3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose
• CAS No.: 1339886-13-3
• Molecular Formula: C₂₀H₂₃FO₅
• Molecular Weight: 362.398

Synonyms:3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose

Chemical Property of 3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose

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Technology Process of 3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose

There total 3 articles about 3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose 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: 84.0%

1,2:5,6-di-O-isopropylidene-3-C-phenylethynyl-α-D-allofuranose (56998-53-9) → 3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose (1339886-13-3)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20 ℃; for 3h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.jfluchem.2011.07.001

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose (1339886-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; hexane / 4 h / -78 °C / Inert atmosphere

2: diethylamino-sulfur trifluoride / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

With diethylamino-sulfur trifluoride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.jfluchem.2011.07.001

Reference yield:

lithium phenylacetylide (4440-01-1) → 3-deoxy-3-fluoro-1,2;5,6-di(O-isopropylidene)-3-C-(phenylethynyl)-α-D-glucofuranose (1339886-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; hexane / 4 h / -78 °C / Inert atmosphere

2: diethylamino-sulfur trifluoride / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

With diethylamino-sulfur trifluoride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.jfluchem.2011.07.001

upstream raw materials:

1,2:5,6-di-O-isopropylidene-3-C-phenylethynyl-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

lithium phenylacetylide

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