4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal

Base Information

• Chemical Name: 4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal
• CAS No.: 108304-75-2
• Molecular Formula: C₃₄H₅₄N₂O₁₄
• Molecular Weight: 714.808

Synonyms:4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal

Chemical Property of 4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal

Chemical Property:

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Technology Process of 4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal

There total 9 articles about 4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal 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:

3,4,6-tri-O-benzyl-2-deoxy-2-dichloroacetamido-D-glucopyranosyl bromide → 4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal (108304-75-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 33 percent / Hg(CN)2 / benzene / 24 h / Ambient temperature

2: Ba(OH)2*8H₂O / 1.) dioxane-water, 100 deg C, 16 h; 2.) pyridine

3: 57 percent / NaH / dioxane; dimethylformamide / 1.17 h

4: H₂ / Pd-black / ethanol / Ambient temperature

5: benzaldehyde dimethyl acetal / dimethylformamide / 0.5 h / 40 °C

With barium dihydroxide; benzaldehyde dimethyl acetal; hydrogen; mercury(II) cyanide; sodium hydride; palladium; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1246/bcsj.59.1411

Reference yield:

4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal (108304-73-0) → 4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal (108304-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-black / ethanol / Ambient temperature

2: benzaldehyde dimethyl acetal / dimethylformamide / 0.5 h / 40 °C

With benzaldehyde dimethyl acetal; hydrogen; palladium; In ethanol; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.59.1411

Reference yield:

2-amino-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-dichloroacetamido-β-D-glucopyranosyl)-2-N:3-O-carbonyl-2-deoxy-5,6-isopropylidene-D-glucose diethyl acetal (70279-97-9) → 4-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-5,6-isopropylidene-3-O-(2-ethoxymethoxymethyl)-D-glucose diethyl acetal (108304-75-2)

Guidance literature:

Multi-step reaction with 4 steps

1: Ba(OH)2*8H₂O / 1.) dioxane-water, 100 deg C, 16 h; 2.) pyridine

2: 57 percent / NaH / dioxane; dimethylformamide / 1.17 h

3: H₂ / Pd-black / ethanol / Ambient temperature

4: benzaldehyde dimethyl acetal / dimethylformamide / 0.5 h / 40 °C

With barium dihydroxide; benzaldehyde dimethyl acetal; hydrogen; sodium hydride; palladium; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.59.1411

upstream raw materials:

toluene-4-sulfonic acid

N-[(1R,2R,3S)-3-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1-diethoxymethyl-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2-methoxy-ethoxymethoxy)-propyl]-acetamide

2-amino-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-dichloroacetamido-β-D-glucopyranosyl)-2-N:3-O-carbonyl-2-deoxy-5,6-isopropylidene-D-glucose diethyl acetal

2-amino-2-N:3-O-carbonyl-2-deoxy-5,6-isopropylidene-D-glucose diethyl acetal

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