(-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine

Base Information

Chemical Name:(-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine
CAS No.:229170-65-4
Molecular Formula:C₂₃H₃₁NO₄
Molecular Weight:385.503
Hs Code.:

Synonyms:(-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine

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Chemical Property of (-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine

Chemical Property:

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Technology Process of (-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine

There total 9 articles about (-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine 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: 77.0%

: 917-54-4
methyllithium

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

: 229170-65-4
(-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine

Guidance literature:: In tetrahydrofuran; diethyl ether; at -70 ℃; for 0.25h;
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

: 229170-65-4
(-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine

Guidance literature:: Multi-step reaction with 9 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

9.1: 77 percent / tetrahydrofuran; diethyl ether / 0.25 h / -70 °C

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; diethyl ether; 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 / 9.1: Methylation;
DOI:10.1021/jo9823240

Reference yield:

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

: 229170-65-4
(-)-(2S,3R,6S)-N-benzyloxycarbonylnupharamine

Guidance literature:: Multi-step reaction with 6 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

6.1: 77 percent / tetrahydrofuran; diethyl ether / 0.25 h / -70 °C

With 1H-imidazole; hydrogenchloride; oxalyl dichloride; hydrogen; potassium carbonate; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetonitrile; 1.1: Etherification / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Oxidation / 4.2: Addition / 5.1: Hydrogenation / 6.1: Methylation;
DOI:10.1021/jo9823240