(-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

Base Information

Chemical Name:(-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine
CAS No.:229170-64-3
Molecular Formula:C₂₃H₂₉NO₅
Molecular Weight:399.487
Hs Code.:

Synonyms:(-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

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Chemical Property of (-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

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Technology Process of (-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

There total 8 articles about (-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine 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: 85.0%

: 229170-63-2
(-)-(2R,3R,6S)-(E)-N-benzyloxycarbonyl-2-(2-ethoxycarbonyl-1-ethenyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

: 229170-64-3
(-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 6h; under 760 Torr;
DOI:10.1021/jo9823240

Reference yield:

: 209160-33-8
(+)-(2S,5S,6R)-1-aza-2-(3-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo[4.3.0]nonane

: 229170-64-3
(-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 96 percent / lithium hexamethyldisilylamide / tetrahydrofuran / 1.5 h / -80 °C

2.1: 89 percent / hydrogen / PtO₂ / ethanol / 8 h / 20 °C

3.1: 95 percent / t-BuOK / tetrahydrofuran / 0.5 h / 0 °C

4.1: 67 percent / imidazole / acetonitrile / 4 h / 20 °C

5.1: 99 percent / K₂CO₃ / acetonitrile; H₂O / 4 h

6.1: 88 percent / HCl / tetrahydrofuran; H₂O / 0.5 h

7.1: (COCl)2; DMSO / CH₂Cl₂ / 1.5 h / -65 °C

7.2: 96 percent / Et₃N / CH₂Cl₂ / 90 h / -15 - 20 °C

8.1: 85 percent / hydrogen / Pd/C / ethanol / 6 h / 20 °C / 760 Torr

With 1H-imidazole; hydrogenchloride; oxalyl dichloride; potassium tert-butylate; hydrogen; potassium carbonate; dimethyl sulfoxide; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 1.1: Addition / 2.1: Hydrogenation / 3.1: Ring cleavage / 4.1: Etherification / 5.1: Substitution / 6.1: Hydrolysis / 7.1: Oxidation / 7.2: Addition / 8.1: Hydrogenation;
DOI:10.1021/jo9823240

Reference yield:

: 229170-58-5
(-)-(2R,3R,6S)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

: 229170-64-3
(-)-(2R,3R,6S)-N-benzyloxycarbonyl-2-(2-ethoxycarbonylethyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 67 percent / imidazole / acetonitrile / 4 h / 20 °C

2.1: 99 percent / K₂CO₃ / acetonitrile; H₂O / 4 h

3.1: 88 percent / HCl / tetrahydrofuran; H₂O / 0.5 h

4.1: (COCl)2; DMSO / CH₂Cl₂ / 1.5 h / -65 °C

4.2: 96 percent / Et₃N / CH₂Cl₂ / 90 h / -15 - 20 °C

5.1: 85 percent / hydrogen / Pd/C / ethanol / 6 h / 20 °C / 760 Torr

With 1H-imidazole; hydrogenchloride; oxalyl dichloride; hydrogen; potassium carbonate; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 1.1: Etherification / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Oxidation / 4.2: Addition / 5.1: Hydrogenation;
DOI:10.1021/jo9823240