N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide

Base Information

• Chemical Name: N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide
• CAS No.: 827608-34-4
• Molecular Formula: C₃₄H₅₀N₂O₁₉
• Molecular Weight: 790.773
• Mol file: 827608-34-4.mol

Synonyms:N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide

Chemical Property of N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide

There total 6 articles about N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide 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:

phenylacetic anhydride (1555-80-2) + 5-amino-2-[2-(4,5-dihydroxy-2-hydroxymethyl-6-pent-4-enoylamino-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4-hydroxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid → N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide (827608-34-4)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 6h;

DOI:10.1021/jm0494422

Reference yield:

4-pentenoic anhydride (63521-92-6) → N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide (827608-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 515 mg / Lindlar catalyst; H₂ / methanol; ethyl acetate / 3 h / 20 °C

2: aq. NaOH / 10 h / 20 °C

3: 20 mg / aq. NaOH / methanol / 6 h / 20 °C

With sodium hydroxide; Lindlar's catalyst; hydrogen; In methanol; ethyl acetate;

DOI:10.1021/jm0494422

Reference yield:

O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (433304-33-7) → N-{O-[5-phenylacetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-β-D-glucopyranosyl} 4-pentenamide (827608-34-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 4A molecular sieves / acetonitrile / 20 h / 20 °C

1.2: NIS; TfOH / acetonitrile / 1 h / -35 °C

2.1: 515 mg / Lindlar catalyst; H₂ / methanol; ethyl acetate / 3 h / 20 °C

3.1: aq. NaOH / 10 h / 20 °C

4.1: 20 mg / aq. NaOH / methanol / 6 h / 20 °C

With sodium hydroxide; Lindlar's catalyst; 4 A molecular sieve; hydrogen; In methanol; ethyl acetate; acetonitrile;

DOI:10.1021/jm0494422

upstream raw materials:

phenylacetic anhydride

4-pentenoic anhydride

O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide

4-acetoxy-2-[3-acetoxy-6-acetoxymethyl-2-(4,5-diacetoxy-2-acetoxymethyl-6-azido-tetrahydro-pyran-3-yloxy)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester