tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate
CAS No.:1356115-92-8
Molecular Formula:C₁₆H₂₃NO₅
Molecular Weight:309.362
Hs Code.:

Synonyms:tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

There total 2 articles about tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-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: 83.0%

: 1356115-73-5
tert-butyl (2S,5R)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

: 1356115-92-8
tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

Guidance literature:: With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 48h; diastereoselective reaction;
DOI:10.1002/ejoc.201100886

Reference yield:

: 501096-26-0
(2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline

: 1356115-92-8
tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol / 3 h / 20 °C / Inert atmosphere

2: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 48 h / 20 °C

With potassium osmate(VI) dihydrate; sodium tetrahydroborate; 4-methylmorpholine N-oxide; calcium chloride; In tetrahydrofuran; ethanol; water; acetone; tert-butyl alcohol;
DOI:10.1002/ejoc.201100886

Reference yield: 80.0%

: 1356115-92-8
tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-phenylpyrrolidine-1-carboxylate

: 77-76-9
2,2-dimethoxy-propane

: 1356115-94-0
tert-butyl (3aR,4R,6S,6aS)-4-(hydroxymethyl)-2,2-dimethyl-6-phenyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 12h; regioselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201100886