5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide

Base Information

Chemical Name:5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide
CAS No.:268539-16-8
Molecular Formula:C₄₉H₆₅N₉O₂₆
Molecular Weight:1196.1
Hs Code.:

Synonyms:5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide

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Chemical Property of 5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide

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Technology Process of 5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide

There total 7 articles about 5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide 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: 66.0%

: 252210-03-0
5-(azidomethyl)benzene-1,3-dicarbonyl dichloride

: Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{2-[2-(2-amino-acetylamino)-acetylamino]-ethoxy}-tetrahydro-pyran-4-yl ester

: 268539-16-8
5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 48h;
DOI:10.1016/S0957-4166(99)00589-3

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-Mannose pentaacetate

: 268539-16-8
5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide

Guidance literature:: Multi-step reaction with 7 steps

1: hydrazine acetate / 50 °C

2: K₂Co₃

3: 53 percent / 4 A molecular sieves; TMSOTf / CH₂Cl₂ / 5 h / 25 °C

4: H₂, / Pd/C / ethanol / 3 h

5: 63 percent / DCC; HOBt / dimethylformamide / 12 h / 25 °C

6: H₂, / Pd/C / ethanol / 2.5 h

7: 66 percent / DCC,; HOBt / CH₂Cl₂ / 48 h / 25 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; hydrazinium monoacetate; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: chloroacetamidation / 3: glycosylation / 4: Hydrogenation / 5: N-alkylation / 6: Hydrogenation / 7: N-acylation;
DOI:10.1016/S0957-4166(99)00589-3

Reference yield:

: 3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1
2,3,4,6-tetra-O-acetyl-D-mannopyranose

: 268539-16-8
5-azidomethyl-N,N'-bis<2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-N-ethylglycylglycyl>benzene-1,3-dicarboxamide

Guidance literature:: Multi-step reaction with 6 steps

1: K₂Co₃

2: 53 percent / 4 A molecular sieves; TMSOTf / CH₂Cl₂ / 5 h / 25 °C

3: H₂, / Pd/C / ethanol / 3 h

4: 63 percent / DCC; HOBt / dimethylformamide / 12 h / 25 °C

5: H₂, / Pd/C / ethanol / 2.5 h

6: 66 percent / DCC,; HOBt / CH₂Cl₂ / 48 h / 25 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; 1: chloroacetamidation / 2: glycosylation / 3: Hydrogenation / 4: N-alkylation / 5: Hydrogenation / 6: N-acylation;
DOI:10.1016/S0957-4166(99)00589-3