(S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

Base Information

Chemical Name:(S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester
CAS No.:239784-37-3
Molecular Formula:C₂₂H₃₃NO₆
Molecular Weight:407.507
Hs Code.:

Synonyms:(S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

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Chemical Property of (S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

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Technology Process of (S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

There total 10 articles about (S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester 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: 66.0%

: 239784-36-2
(S)-2-((3aR,7R,7aR)-7-Benzyloxy-2,2-dimethyl-4-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-yl)-4-methyl-pentanoic acid tert-butyl ester

: 239784-37-3
(S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; for 24h; Heating;
DOI:10.1016/S0040-4039(99)00897-7

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 239784-37-3
(S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

2: 2,6-lutidine / CH₂Cl₂ / 12 h / Ambient temperature

3: 90 percent / NaOAc / methanol / 48 h / Heating

4: 70 percent / K₂CO₃, KI / acetonitrile / 32 h / Heating

5: 66 percent / PPTS / methanol / 24 h / Heating

With 2,6-dimethylpyridine; sodium acetate; pyridinium p-toluenesulfonate; potassium carbonate; potassium iodide; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(99)00897-7

Reference yield:

: 96239-82-6
2,3-O-isopropylidene-5-iodo-D-ribono-1,4-lactone

: 239784-37-3
(S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / 2,6-lutidine / CH₂Cl₂ / Heating

2: K₂CO₃ / acetonitrile / Heating

3: NaH / tetrahydrofuran

4: 70 percent / K₂CO₃, KI / acetonitrile / 32 h / Heating

5: 66 percent / PPTS / methanol / 24 h / Heating

With 2,6-dimethylpyridine; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; potassium iodide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(99)00897-7