3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

Base Information

Chemical Name:3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine
CAS No.:419573-42-5
Molecular Formula:C₅₂H₇₂N₄O₁₇Si
Molecular Weight:1053.25
Hs Code.:

Synonyms:3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

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Chemical Property of 3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

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Technology Process of 3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

There total 8 articles about 3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-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: 96.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 419573-41-4
3,2',6'-tris(N-benzyloxycarbonyl)-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

: 419573-42-5
3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/ja011695m

Reference yield:

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

: 419573-42-5
3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja011695m

Reference yield:

: 3947-65-7
neomycin A

: 419573-42-5
3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja011695m