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

Base Information

Chemical Name:(-)-(2R,3R,6S)-(E)-N-benzyloxycarbonyl-2-(2-ethoxycarbonyl-1-ethenyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine
CAS No.:229170-63-2
Molecular Formula:C₂₃H₂₇NO₅
Molecular Weight:397.471
Hs Code.:

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

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Chemical Property of (-)-(2R,3R,6S)-(E)-N-benzyloxycarbonyl-2-(2-ethoxycarbonyl-1-ethenyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

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Technology Process of (-)-(2R,3R,6S)-(E)-N-benzyloxycarbonyl-2-(2-ethoxycarbonyl-1-ethenyl)-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

There total 7 articles about (-)-(2R,3R,6S)-(E)-N-benzyloxycarbonyl-2-(2-ethoxycarbonyl-1-ethenyl)-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: 96.0%

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 229170-62-1
(-)-(2R,3R,6S)-N-benzyloxycarbonyl-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine

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

Guidance literature:: (-)-(2R,3R,6S)-N-benzyloxycarbonyl-6-(3-furyl)-2-hydroxymethyl-3-methylpiperidine; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -65 ℃; for 1.5h;

ethyl (triphenylphosphoranylidene)acetate; With triethylamine; In dichloromethane; at -15 - 20 ℃; for 90h;
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

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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; hydrogenchloride; oxalyl dichloride; potassium tert-butylate; hydrogen; potassium carbonate; dimethyl sulfoxide; lithium hexamethyldisilazane; platinum(IV) oxide; 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;
DOI:10.1021/jo9823240

Reference yield:

: 229170-66-5
Trifluoro-methanesulfonic acid (5S,8S,8aR)-5-furan-3-yl-8-methyl-3-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-7-yl ester

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

Guidance literature:: Multi-step reaction with 6 steps

1.1: 89 percent / hydrogen / PtO₂ / ethanol / 8 h / 20 °C

2.1: 95 percent / t-BuOK / tetrahydrofuran / 0.5 h / 0 °C

3.1: 67 percent / imidazole / acetonitrile / 4 h / 20 °C

4.1: 99 percent / K₂CO₃ / acetonitrile; H₂O / 4 h

5.1: 88 percent / HCl / tetrahydrofuran; H₂O / 0.5 h

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

6.2: 96 percent / Et₃N / CH₂Cl₂ / 90 h / -15 - 20 °C

With 1H-imidazole; hydrogenchloride; oxalyl dichloride; potassium tert-butylate; hydrogen; potassium carbonate; dimethyl sulfoxide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 1.1: Hydrogenation / 2.1: Ring cleavage / 3.1: Etherification / 4.1: Substitution / 5.1: Hydrolysis / 6.1: Oxidation / 6.2: Addition;
DOI:10.1021/jo9823240