methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate
• CAS No.: 1304780-12-8
• Molecular Formula: C₂₇H₃₅N₃O₁₂S
• Molecular Weight: 625.654

Synonyms:methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate

Chemical Property of methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate

Chemical Property:

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Technology Process of methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate

There total 6 articles about methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-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: 64.0%

phenylacetylene (536-74-3) + Methanesulfonyl azide (624-90-8,1516-70-7) + 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester (139110-70-6) → methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate (1304780-12-8)

Guidance literature:

With copper(l) iodide; triethylamine; In chloroform; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.02.010

Reference yield:

N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) → methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate (1304780-12-8)

Guidance literature:

Multi-step reaction with 6 steps

1: Amberlite IR₁₂₀ (H⁺)

2: pyridine

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

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

5: hydrogen / ethanol / 9 h / 20 °C

6: copper(l) iodide; triethylamine / chloroform / 1 h / 20 °C / Inert atmosphere

With pyridine; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; hydrogen; triethylamine; In ethanol; chloroform; ethyl acetate; tert-butyl alcohol;

DOI:10.1016/j.bmc.2011.02.010

Reference yield:

N-acetylneuraminic acid methyl ester (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2) → methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate (1304780-12-8)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine

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

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

4: hydrogen / ethanol / 9 h / 20 °C

5: copper(l) iodide; triethylamine / chloroform / 1 h / 20 °C / Inert atmosphere

With pyridine; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; hydrogen; triethylamine; In ethanol; chloroform; ethyl acetate; tert-butyl alcohol;

DOI:10.1016/j.bmc.2011.02.010

upstream raw materials:

N-acetyl neuraminic acid

N-acetylneuraminic acid methyl ester

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

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Downstream raw materials:

5-acetamido-2,6-anhydro-3,5-dideoxy-4-[2-(4-fluorophenyl)-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonic acid

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