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

Base Information

• Chemical Name: 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
• CAS No.: 260365-18-2
• Molecular Formula: C₄₉H₆₆N₄O₂₆
• Molecular Weight: 1127.07

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 2 articles about 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 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:

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-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-acetyl-β-D-galactopyranosyl]-β-alanine (260365-18-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With hydrogen; 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;

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) + 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 (260365-24-0) → 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)

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 22h;

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

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

upstream raw materials:

3-(benzyloxycarbonylamino)propanoic acid

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

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

Downstream raw materials:

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

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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