(2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate

Base Information

Chemical Name:(2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate
CAS No.:1187433-84-6
Molecular Formula:C₁₄H₁₇FO₅
Molecular Weight:284.284
Hs Code.:

Synonyms:(2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate

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Chemical Property of (2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate

Chemical Property:

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Technology Process of (2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate

There total 2 articles about (2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-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:

: ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

: 67-56-1
methanol

: 1187433-84-6
(2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate

: 914377-19-8
((2R,3R,4R)-3-benzoyloxy-4-fluoro-5-methoxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

Guidance literature:: ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate; methanol; With boron trifluoride diethyl etherate; at 20 - 80 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In methanol; Inert atmosphere;
DOI:10.1016/j.bmc.2010.07.017

Reference yield:

: 874638-80-9,1033394-94-3
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

: 1187433-84-6
(2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate

: 914377-19-8
((2R,3R,4R)-3-benzoyloxy-4-fluoro-5-methoxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / -10 - 0 °C

2: boron trifluoride diethyl etherate / 20 - 80 °C

With boron trifluoride diethyl etherate; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran;

Reference yield:

: 1187433-84-6
(2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyltetrahydrofuran-3-yl benzoate

: ((2R,4R)-3-acetoxy-5-(2-amino-6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: ammonia / 36 h / 20 °C

2.1: 1H-imidazole / dichloromethane / 0 - 20 °C

3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: diethyl ether / 4.5 h / 0 - 20 °C

5.1: tetrabutyl ammonium fluoride; water / tetrahydrofuran / 1.67 h / 0 - 20 °C

6.1: dmap; triethylamine / dichloromethane / 0 °C

6.2: 0 - 45 °C

7.1: sulfuric acid / acetic acid / 0 - 20 °C

8.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 20 °C / Reflux

8.2: 0 °C / Reflux

With 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; tetrabutyl ammonium fluoride; ammonia; water; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; acetonitrile;