N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 131204-10-9
• Molecular Formula: C₃₂H₄₃NO₁₂
• Molecular Weight: 633.693

Synonyms:N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

There total 6 articles about N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-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: 95.0%

allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (131204-07-4) → N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (131204-10-9)

Guidance literature:

With sodium methylate; In methanol; for 24h; Ambient temperature;

DOI:10.1016/0008-6215(90)80134-O

Reference yield:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) → N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (131204-10-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 92.2 percent / p-toluenesulfonic acid / dimethylformamide / 24 h / Ambient temperature

2: 98.5 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 12 h / Ambient temperature

3: 97.2 percent / pyridinium p-toluenesulfonate / methanol / 0.17 h / Heating

4: 1) dibutyltin oxide, 2) tetrabutylammonium iodide / 1) benzene, 3 h, reflux, 2) 45-50 deg C, 6 h

5: 64.7 percent / 4 Angstroem molecular sieves / mercury(II) cyanide / nitromethane; toluene / 4 h / Ambient temperature

6: 95 percent / sodium methoxide / methanol / 24 h / Ambient temperature

With barium hydroxide octahydrate; 4 A molecular sieve; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; barium(II) oxide; mercury(II) cyanide; In methanol; nitromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(90)80134-O

Reference yield:

allyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside (131204-04-1) → N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (131204-10-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 97.2 percent / pyridinium p-toluenesulfonate / methanol / 0.17 h / Heating

2: 1) dibutyltin oxide, 2) tetrabutylammonium iodide / 1) benzene, 3 h, reflux, 2) 45-50 deg C, 6 h

3: 64.7 percent / 4 Angstroem molecular sieves / mercury(II) cyanide / nitromethane; toluene / 4 h / Ambient temperature

4: 95 percent / sodium methoxide / methanol / 24 h / Ambient temperature

With 4 A molecular sieve; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; mercury(II) cyanide; In methanol; nitromethane; toluene;

DOI:10.1016/0008-6215(90)80134-O

upstream raw materials:

allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside

allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

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