(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate
CAS No.:1404101-23-0
Molecular Formula:C₁₆H₁₉NO₆
Molecular Weight:321.33
Hs Code.:

Synonyms:(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

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Chemical Property of (S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

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Technology Process of (S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

There total 6 articles about (S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate 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: 61.0%

: 1407965-69-8
(S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate

: 1404101-23-0
(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 0 ℃; for 3h;
DOI:10.1016/j.tetlet.2012.08.061

Reference yield:

: 1407965-69-8
(S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate

: 1404101-23-0
(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

: 1404101-17-2
(S)-benzyl 2-((2S,3R,4R)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 6h; Overall yield = 71 %; Overall yield = 102.7 mg;
DOI:10.1021/jo301967w

Reference yield:

: 146118-95-8
benzyl (S)-2-{[methoxy(methyl)amino]carbonyl}pyrrolidine-1-carboxylate

: 1404101-23-0
(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

2: tetrahydrofuran / 3 h / 0 °C

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / 20 °C

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; water / 3 h / 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; lithium aluminium tetrahydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone; toluene;
DOI:10.1016/j.tetlet.2012.08.061