2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Base Information

Chemical Name:2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol
CAS No.:114040-91-4
Molecular Formula:C₂₃H₂₈N₄O₃
Molecular Weight:408.5
Hs Code.:

Synonyms:2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

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Chemical Property of 2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

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Technology Process of 2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

There total 10 articles about 2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 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:

: N-Benzyl-3-O-benzyl-4,6-O-isopropylidene-2-trifluoromethanesulphonyl-1,5-dideoxy-1,5-imino-D-mannitol

: 114040-91-4
2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: In N-methyl-acetamide; dichloromethane; toluene;

Reference yield:

: 114040-90-3
N-benzyl-3-O-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-2-O-(trifluoro-methyl)sulfonyl-D-mannitol

: 114040-91-4
2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: With lithium azide; In dichloromethane; N,N-dimethyl-formamide; at -40 ℃; for 8h;
DOI:10.1016/0008-6215(87)80126-X

Reference yield:

: 19130-96-2
1,5-dideoxy-1,5-imino-D-glucitol

: 114040-91-4
2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: Multi-step reaction with 8 steps

1: potassium carbonate / dimethylformamide / 2 h

2: 249.3 g / p-toluenesulfonic acid / dimethylformamide; various solvent(s) / 2 h / 30 °C

3: 97 percent / triethylamine / acetone / 6 h / Ambient temperature

4: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C

5: 75 percent / N-methylmorpholine N-oxide hydrate, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol

6: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h

7: 95 percent / pyridine / CH₂Cl₂ / 1 h

8: 10.6 g / lithium azide / CH₂Cl₂; dimethylformamide / 8 h / -40 °C

With pyridine; osmium(VIII) oxide; lithium azide; tetrabutylammomium bromide; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; zinc; In dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/0008-6215(87)80126-X