N³-Benzyloxycarbonyl-N¹-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide

Base Information

• Chemical Name: N³-Benzyloxycarbonyl-N¹-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide
• CAS No.: 260365-19-3
• Molecular Formula: C₃₃H₅₀N₄O₁₈
• Molecular Weight: 790.776

Synonyms:N³-Benzyloxycarbonyl-N¹-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide

Chemical Property of N³-Benzyloxycarbonyl-N¹-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide

Chemical Property:

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Technology Process of N³-Benzyloxycarbonyl-N¹-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide

There total 4 articles about N³-Benzyloxycarbonyl-N¹-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide 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: 86.0%

N3-Benzyloxycarbonyl-N1-[3,6-bis-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-acetyl-β-D-galactopyranosyl]-β-alanine (260365-18-2) → N3-Benzyloxycarbonyl-N1-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide (260365-19-3)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 18h;

DOI:10.1002/(SICI)1521-3765(20000103)6:1<162::AID-CHEM162>3.0.CO;2-9

Reference yield:

3,6-Bis-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-acetyl-β-D-galactopyranosyl azide (260365-17-1) → N3-Benzyloxycarbonyl-N1-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide (260365-19-3)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10 percent Pd/C / methanol / 0.5 h / 0 °C / 760 Torr

2: HOBt; DIEA; HBTU / tetrahydrofuran / 22 h / 20 °C

3: 86 percent / NaOMe; MeOH / 18 h / 20 °C

With methanol; hydrogen; sodium methylate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Catalytic hydrogenation / 2: Acylation / 3: Deacetylation;

DOI:10.1002/(SICI)1521-3765(20000103)6:1<162::AID-CHEM162>3.0.CO;2-9

Reference yield:

3-(benzyloxycarbonylamino)propanoic acid (2304-94-1) → N3-Benzyloxycarbonyl-N1-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide (260365-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HOBt; DIEA; HBTU / tetrahydrofuran / 22 h / 20 °C

2: 86 percent / NaOMe; MeOH / 18 h / 20 °C

With methanol; sodium methylate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1: Acylation / 2: Deacetylation;

DOI:10.1002/(SICI)1521-3765(20000103)6:1<162::AID-CHEM162>3.0.CO;2-9

upstream raw materials:

N³-Benzyloxycarbonyl-N¹-[3,6-bis-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-acetyl-β-D-galactopyranosyl]-β-alanine

3-(benzyloxycarbonylamino)propanoic acid

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

acetic acid 5-acetoxy-6-amino-4-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

N³-Benzyloxycarbonyl-N¹-{3,6-bis-O-[β-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-β-D-galactopyranosyl}-β-alanine amide

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