N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 74615-22-8
• Molecular Formula: C₅₆H₆₁NO₁₂
• Molecular Weight: 940.1

Synonyms:N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

There total 1 articles about N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-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: 82.0%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside (74615-21-7) → N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (74615-22-8) + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-arabino-hexopyranosyl-2-ulose)-α-D-glucopyranoside (74615-24-0)

Guidance literature:

With dimethyl sulfoxide; In acetic acid; Ambient temperature;

DOI:10.1016/S0008-6215(00)85521-4

Reference yield:

N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (74615-22-8) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside (74615-23-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; for 4h; Yield given; Ambient temperature;

DOI:10.1016/S0008-6215(00)85521-4

Reference yield:

N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3,3-dihydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (74615-22-8) → 2-acetamido-2-deoxy-4-O-(β-D-mannopyranosyl)-β-D-glucosamine (186765-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium borohydride / CH₂Cl₂; methanol / 4 h / Ambient temperature

2: 90 percent / H₂ / palladium-on-charcoal (10percent) / acetic acid / 48 h / 1520 Torr / Ambient temperature

With sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In methanol; dichloromethane; acetic acid;

DOI:10.1016/S0008-6215(00)85521-4

upstream raw materials:

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Downstream raw materials:

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

2-acetamido-2-deoxy-4-O-(β-D-mannopyranosyl)-β-D-glucosamine

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