methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate
• CAS No.: 1445461-04-0
• Molecular Formula: C₂₉H₃₇N₃O₁₂
• Molecular Weight: 619.626
• Mol file: 1445461-04-0.mol

Synonyms:

Chemical Property of methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate

There total 4 articles about methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate 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: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + methyl 5-acetamido-7,8,9-tri-O-acetyl-2,3-didehydro-2,3,4,5-tetradeoxy-4-formamido-D-glycero-D-galacto-2-nonulopyranosidonate (130525-60-9) + acetic acid (64-19-7,77671-22-8) + benzylamine (100-46-9) → methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate (1445461-04-0)

Guidance literature:

formaldehyd; benzylamine; In methanol; water; at 20 ℃; for 0.166667h;

methyl 5-acetamido-7,8,9-tri-O-acetyl-2,3-didehydro-2,3,4,5-tetradeoxy-4-formamido-D-glycero-D-galacto-2-nonulopyranosidonate; acetic acid; In methanol; water; at 20 ℃; for 0.5h;

DOI:10.1248/cpb.c12-00834

Reference yield:

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (6931-68-6,72690-21-2,74006-95-4,108740-37-0,108740-38-1,108740-39-2,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,73208-82-9) → methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate (1445461-04-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 50 °C

2.1: trimethylsilylazide / tert-butyl alcohol / 9 h / Reflux

3.1: hydrogen; triethylamine / ethyl acetate / 48 h / 20 °C

4.1: 17 h / 20 °C

5.1: methanol; water / 0.17 h / 20 °C

5.2: 0.5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; hydrogen; triethylamine; In methanol; water; ethyl acetate; tert-butyl alcohol; 5.1: |Ugi Condensation / 5.2: |Ugi Condensation;

DOI:10.1248/cpb.c12-00834

Reference yield:

methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate (78850-37-0) → methyl 5-scetylamino-2,6-anhydro-3,5-dideoxy-4-[2-(acetylbenzylamino)acetylamino]-D-glycero-D-galacto-non-2-enonate (1445461-04-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trimethylsilylazide / tert-butyl alcohol / 9 h / Reflux

2.1: hydrogen; triethylamine / ethyl acetate / 48 h / 20 °C

3.1: 17 h / 20 °C

4.1: methanol; water / 0.17 h / 20 °C

4.2: 0.5 h / 20 °C

With trimethylsilylazide; hydrogen; triethylamine; In methanol; water; ethyl acetate; tert-butyl alcohol; 4.1: |Ugi Condensation / 4.2: |Ugi Condensation;

DOI:10.1248/cpb.c12-00834

upstream raw materials:

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

formaldehyd

methyl 5-acetamido-7,8,9-tri-O-acetyl-2,3-didehydro-2,3,4,5-tetradeoxy-4-formamido-D-glycero-D-galacto-2-nonulopyranosidonate

Downstream raw materials:

C₂₂H₂₉N₃O₉