2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine

Base Information

Chemical Name:2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine
CAS No.:80887-38-3
Molecular Formula:C₄₄H₄₉N₃O₁₀
Molecular Weight:779.887
Hs Code.:

Synonyms:2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine

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Chemical Property of 2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine

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Technology Process of 2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine

There total 9 articles about 2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine 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:

: 100-39-0
benzyl bromide

: 80887-38-3
2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 2 h / Ambient temperature; 1.) N,N-dimethylformamide, RT, 2 h, 2.) chloroform, reflux, 2 h

2: 78 percent / 60 percent aq. acetic acid / 2 h / 90 - 95 °C

3: 84 percent / pyridine / 30 h / Ambient temperature

4: 89 percent / NaOH / dimethylformamide / 5 h / Ambient temperature

5: 79 percent / 60 percent aq. acetic acid / 2 h / 90 °C

6: 56 percent / KOH / benzene; dimethylformamide / 3 h / Ambient temperature

7: 1.) NaBH₄, 2.) dicyclohexylcarbondiimide / 1.) DMF, 6 h, 0 deg C, 2.) CH₂Cl₂, RT, 16 h

With pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; acetic acid; dicyclohexyl-carbodiimide; barium(II) oxide; In N,N-dimethyl-formamide; benzene;
DOI:10.1246/bcsj.54.3570

Reference yield:

: 29847-23-2
2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide

: 80887-38-3
2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 8 steps

1: 76 percent / formic acid / 0.5 h / Ambient temperature

2: 82 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 2 h / Ambient temperature; 1.) N,N-dimethylformamide, RT, 2 h, 2.) chloroform, reflux, 2 h

3: 78 percent / 60 percent aq. acetic acid / 2 h / 90 - 95 °C

4: 84 percent / pyridine / 30 h / Ambient temperature

5: 89 percent / NaOH / dimethylformamide / 5 h / Ambient temperature

6: 79 percent / 60 percent aq. acetic acid / 2 h / 90 °C

7: 56 percent / KOH / benzene; dimethylformamide / 3 h / Ambient temperature

8: 1.) NaBH₄, 2.) dicyclohexylcarbondiimide / 1.) DMF, 6 h, 0 deg C, 2.) CH₂Cl₂, RT, 16 h

With pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; formic acid; barium hydroxide octahydrate; acetic acid; dicyclohexyl-carbodiimide; barium(II) oxide; In N,N-dimethyl-formamide; benzene;
DOI:10.1246/bcsj.54.3570

Reference yield:

: 80887-28-1
2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

: 80887-38-3
2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / pyridine / 30 h / Ambient temperature

2: 89 percent / NaOH / dimethylformamide / 5 h / Ambient temperature

3: 79 percent / 60 percent aq. acetic acid / 2 h / 90 °C

4: 56 percent / KOH / benzene; dimethylformamide / 3 h / Ambient temperature

5: 1.) NaBH₄, 2.) dicyclohexylcarbondiimide / 1.) DMF, 6 h, 0 deg C, 2.) CH₂Cl₂, RT, 16 h

With pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; acetic acid; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; benzene;
DOI:10.1246/bcsj.54.3570