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

Base Information

• Chemical Name: 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
• CAS No.: 260365-20-6
• Molecular Formula: C₄₅H₇₀N₄O₂₈
• Molecular Weight: 1115.06

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of 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

There total 5 articles about 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 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: 100.0%

uridine 5'-diphospho-D-galactose (2956-16-3) + N3-Benzyloxycarbonyl-N1-[3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranosyl]-β-alanine amide (260365-19-3) → 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 (260365-20-6)

Guidance literature:

With HEPES buffer; manganese(ll) chloride; β-1,4-galactosyltransferase; alkaline phosphatase from bovine intestinal mucosa; In water; at 37 ℃; for 12h; pH=7.0;

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-[β-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-β-D-galactopyranosyl}-β-alanine amide (260365-20-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 100 percent / HEPES buffer; MnCl2*4H2O / β-1,4-galactosyltransferase; alkaline phosphatase from bovine intestinal mucosa, P-2276 / H2O / 12 h / 37 °C / pH 7.0

With methanol; HEPES buffer; sodium methylate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; manganese(ll) chloride; β-1,4-galactosyltransferase; alkaline phosphatase from bovine intestinal mucosa; In tetrahydrofuran; water; 1: Acylation / 2: Deacetylation / 3: Esterification;

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-[β-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-β-D-galactopyranosyl}-β-alanine amide (260365-20-6)

Guidance literature:

Multi-step reaction with 4 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

4: 100 percent / HEPES buffer; MnCl2*4H2O / β-1,4-galactosyltransferase; alkaline phosphatase from bovine intestinal mucosa, P-2276 / H2O / 12 h / 37 °C / pH 7.0

With methanol; HEPES buffer; hydrogen; sodium methylate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; manganese(ll) chloride; palladium on activated charcoal; β-1,4-galactosyltransferase; alkaline phosphatase from bovine intestinal mucosa; In tetrahydrofuran; methanol; water; 1: Catalytic hydrogenation / 2: Acylation / 3: Deacetylation / 4: Esterification;

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

upstream raw materials:

uridine 5'-diphospho-D-galactose

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

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

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