(2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

Base Information

Chemical Name:(2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol
CAS No.:1187433-88-0
Molecular Formula:C₂₄H₃₃FO₄Si
Molecular Weight:432.608
Hs Code.:

Synonyms:(2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

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Chemical Property of (2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

Chemical Property:

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Technology Process of (2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

There total 7 articles about (2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol 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:

: 1187433-87-9
(2R,4S)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-4-methyl-dihydrofuran-3(2H)-one

: 75-16-1
methylmagnesium bromide

: 1187433-88-0
(2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

: 1187433-89-1
(2R,3R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

Guidance literature:: (2R,4S)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-4-methyl-dihydrofuran-3(2H)-one; methylmagnesium bromide; In diethyl ether; at 0 - 20 ℃; for 4.5h; Inert atmosphere;

With water; ammonium chloride; In diethyl ether; optical yield given as %de; Inert atmosphere;
DOI:10.1016/j.bmc.2010.07.017

Reference yield:

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

: 1187433-88-0
(2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

: 1187433-89-1
(2R,3R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

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

2: ammonia / 36 h / 20 °C

3: 1H-imidazole / dichloromethane / 0 - 20 °C

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

5: diethyl ether / 4.5 h / 0 - 20 °C

With 1H-imidazole; boron trifluoride diethyl etherate; ammonia; Dess-Martin periodane; In diethyl ether; dichloromethane;

Reference yield:

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

: 1187433-88-0
(2R,3S,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

: 1187433-89-1
(2R,3R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyltetrahydrofuran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: ammonia / 36 h / 20 °C

4: 1H-imidazole / dichloromethane / 0 - 20 °C

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

6: diethyl ether / 4.5 h / 0 - 20 °C

With 1H-imidazole; boron trifluoride diethyl etherate; ammonia; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; diethyl ether; dichloromethane;