6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

Base Information

Chemical Name:6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine
CAS No.:419573-49-2
Molecular Formula:C₆₀H₈₂N₆O₁₉
Molecular Weight:1191.34
Hs Code.:

6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

Synonyms:6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

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Chemical Property of 6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

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Technology Process of 6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

There total 14 articles about 6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine 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: 67.0%

: 46460-73-5
N-benzyloxycarbonyl-1,3-diaminopropane

: 419573-47-0
3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethyl-6-O-(2-oxoethyl)neamine

: 419573-49-2
6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

Guidance literature:: With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 2h;
DOI:10.1021/ja011695m

Reference yield:

: 22854-75-7
N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine

: 419573-49-2
6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

Guidance literature:: Multi-step reaction with 12 steps

1: 56.6 percent / TsOH / dimethylformamide / 36 h / 20 °C

2: 79 percent / Bu₄NI; (i-Pr)2NEt / dimethylformamide / 40 h / 32 °C

3: 95 percent / AcOH / dioxane; H₂O / 10 h / 60 - 65 °C

4: 89 percent / NaH / dimethylformamide / 3 h / 20 °C

5: 80 percent / imidazole; DMAP; triethylamine / dimethylformamide / 5 h / 20 °C

6: 96 percent / Et₃N; DMAP / tetrahydrofuran / 4 h / 20 °C

7: 85 percent / TBAF / tetrahydrofuran / 0.17 h / ice bath

8: 97 percent / Bu₄NI; (i-Pr)2NEt / dimethylformamide / 34 h / 32 °C

9: 88 percent / aq. LiOH / dioxane / 0.5 h / 20 °C

10: 69 percent / Bu₄NI; (Me₃Si)2NLi / dimethylsulfoxide; tetrahydrofuran / 1 h / 20 °C

11: 81 percent / O₃ / CH₂Cl₂ / -78 °C

12: 67 percent / NaBH₃CN; AcOH / methanol / 2 h / 20 °C

With 1H-imidazole; dmap; lithium hydroxide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja011695m

Reference yield:

: 3947-65-7
neomycin A

: 419573-49-2
6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine

Guidance literature:: Multi-step reaction with 13 steps

1: 95 percent / aq. Na₂CO₃ / acetone

2: 56.6 percent / TsOH / dimethylformamide / 36 h / 20 °C

3: 79 percent / Bu₄NI; (i-Pr)2NEt / dimethylformamide / 40 h / 32 °C

4: 95 percent / AcOH / dioxane; H₂O / 10 h / 60 - 65 °C

5: 89 percent / NaH / dimethylformamide / 3 h / 20 °C

6: 80 percent / imidazole; DMAP; triethylamine / dimethylformamide / 5 h / 20 °C

7: 96 percent / Et₃N; DMAP / tetrahydrofuran / 4 h / 20 °C

8: 85 percent / TBAF / tetrahydrofuran / 0.17 h / ice bath

9: 97 percent / Bu₄NI; (i-Pr)2NEt / dimethylformamide / 34 h / 32 °C

10: 88 percent / aq. LiOH / dioxane / 0.5 h / 20 °C

11: 69 percent / Bu₄NI; (Me₃Si)2NLi / dimethylsulfoxide; tetrahydrofuran / 1 h / 20 °C

12: 81 percent / O₃ / CH₂Cl₂ / -78 °C

13: 67 percent / NaBH₃CN; AcOH / methanol / 2 h / 20 °C

With 1H-imidazole; dmap; lithium hydroxide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; sodium carbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja011695m