(3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one

Base Information

Chemical Name:(3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one
CAS No.:1583260-49-4
Molecular Formula:C₁₃H₁₅FO₄
Molecular Weight:254.258
Hs Code.:

Synonyms:(3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one

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Chemical Property of (3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one

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Technology Process of (3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one

There total 2 articles about (3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one 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:

: 3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

: 1583260-49-4
(3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: water; titanium(IV) dichlorodiisopropylate / dichloromethane / 20 h / -20 °C / Inert atmosphere

2.1: zinc; acetic acid / ethyl acetate; ethanol; water / 2 h / 20 °C / Sonication

2.2: 24 h / 20 °C

With titanium(IV) dichlorodiisopropylate; water; acetic acid; zinc; In ethanol; dichloromethane; water; ethyl acetate; 1.1: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q

Reference yield:

: 1583260-48-3
(2R,3R,4R)-isopropyl 5-(benzyloxy)-2-fluoro-3-hydroxy-2-methyl-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

: 1583260-49-4
(3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one

: (3S,4S,5S)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one

Guidance literature:: (2R,3R,4R)-isopropyl 5-(benzyloxy)-2-fluoro-3-hydroxy-2-methyl-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate; With acetic acid; zinc; In ethanol; water; ethyl acetate; at 20 ℃; for 2h; Sonication;

With trifluoroacetic acid; In toluene; at 20 ℃; for 24h; Overall yield = 80 %; Overall yield = 667 mg; diastereoselective reaction;
DOI:10.1021/ja502205q