N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 643734-61-6
• Molecular Formula: C₂₃H₃₇NO₆Si
• Molecular Weight: 451.635

Synonyms:N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

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Technology Process of N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide

There total 3 articles about N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-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: 60.0%

N-((2S,3R,4R,5S,6R)-4-Benzyloxy-6-cyanomethyl-2-methoxy-5-triethylsilanyloxy-tetrahydro-pyran-3-yl)-acetamide (643734-60-5) → ((2R,3S,4R,5R,6S)-4-Benzyloxy-5-ethylamino-6-methoxy-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-acetaldehyde + N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide (643734-61-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1002/anie.200351969

Reference yield:

N-((2S,3R,4R,5S,6R)-4-Benzyloxy-6-cyanomethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl)-acetamide (643734-59-2) → N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide (643734-61-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 60 percent / diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

With pyridine; dmap; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1002/anie.200351969

Reference yield:

C17H21N2O8S(1-)*Na(1+) → N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-6-(2-oxo-ethyl)-5-triethylsilanyloxy-tetrahydro-pyran-3-yl]-acetamide (643734-61-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / H₂SO₄; H₂O / tetrahydrofuran / 1 h / 25 °C

2: 80 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 60 percent / diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

With pyridine; dmap; sulfuric acid; water; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.200351969

upstream raw materials:

N-((2S,3R,4R,5S,6R)-4-Benzyloxy-6-cyanomethyl-2-methoxy-5-triethylsilanyloxy-tetrahydro-pyran-3-yl)-acetamide

N-((2S,3R,4R,5S,6R)-4-Benzyloxy-6-cyanomethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl)-acetamide

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