N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Base Information

• Chemical Name: N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide
• CAS No.: 372524-69-1
• Molecular Formula: C₂₈H₄₃NO₁₇
• Molecular Weight: 665.646

Synonyms:N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Chemical Property of N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

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Technology Process of N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

There total 1 articles about N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide 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: 97.0%

(4-O-acetoxymethyl)-benzyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-N-acetamido-β-D-glucopyranosyl)-4-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]-6-O-acetyl-2-O-benzoyl-β-D-galactopyranoside (372524-68-0) → N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide (372524-69-1)

Guidance literature:

With sodium methylate; In methanol; for 16h;

DOI:10.1016/S0040-4020(01)00582-8

Reference yield:

N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide (372524-69-1) → C45H69N2O30(1-)*Na(1+)

Guidance literature:

Multi-step reaction with 2 steps

1: HEPES buffer; MnCl₂; GalE-LgtB / 2 h / 37 °C / pH 7.5 / Enzymatic reaction

2: 38 percent / CMP; CMP-Neu₅Ac synthetase/sialyltransferase; aq. NaOH / HEPES buffer; MgCl₂ / 3 h / 37 °C / pH 7.0 / Enzymatic reaction

With sodium hydroxide; CMP-Neu₅Ac synthetase; GalE-LgtB; HEPES buffer; sialyltransferase; phenkapton; manganese(ll) chloride; HEPES buffer; magnesium chloride;

DOI:10.1016/S0040-4020(01)00582-8

Reference yield:

UDP-glucose (133-89-1) + N-{4,5-dihydroxy-2-[3-hydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-benzyloxy)-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide (372524-69-1) → C34H53NO22

Guidance literature:

With GalE-LgtB; HEPES buffer; manganese(ll) chloride; at 37 ℃; for 2h; pH=7.5; Enzymatic reaction;

DOI:10.1016/S0040-4020(01)00582-8

upstream raw materials:

(4-O-acetoxymethyl)-benzyl 3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-N-acetamido-β-D-glucopyranosyl)-4-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]-6-O-acetyl-2-O-benzoyl-β-D-galactopyranoside

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