4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 137362-90-4
• Molecular Formula: C₂₈H₃₉Cl₂NO₁₁
• Molecular Weight: 636.524

Synonyms:4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of 4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Useful:

Technology Process of 4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 4 articles about 4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 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:

methyl α-L-evernitroside (65827-72-7,65827-77-2,72398-09-5,72398-10-8,83497-41-0,86427-76-1,98712-70-0) → 4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (137362-90-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) 0.05 M aq. H₂SO₄, 2) pyridine / 1) aq. dioxane, 90 deg C, 28 h; 2) room temperature, overnight

2: 73 percent / TMS triflate, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -78 °C

3: 85 percent / H₂ / 10percent Pd/C / various solvent(s) / 1 h

4: 72 percent / Al amalgam / aq. ethanol / 3 h / Ambient temperature

5: 0.64 g / NEt₃ / CH₂Cl₂ / 1 h

With pyridine; aluminum amalgam; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jo00025a034

Reference yield:

methyl 4-O-(4-benzyloxy-3,5-dichloro-2-methoxy-6-methylbenzoyl)-3-O-(2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-α-L-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside (137362-89-1) → 4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (137362-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / H₂ / 10percent Pd/C / various solvent(s) / 1 h

2: 72 percent / Al amalgam / aq. ethanol / 3 h / Ambient temperature

3: 0.64 g / NEt₃ / CH₂Cl₂ / 1 h

With aluminum amalgam; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jo00025a034

Reference yield:

2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-1-O-(p-nitrobenzoyl)-α-L-arabino-hexopyranose (137333-06-3) → 4-Acetoxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-((2S,4S,5R,6S)-4-acetylamino-5-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (137362-90-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / TMS triflate, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -78 °C

2: 85 percent / H₂ / 10percent Pd/C / various solvent(s) / 1 h

3: 72 percent / Al amalgam / aq. ethanol / 3 h / Ambient temperature

4: 0.64 g / NEt₃ / CH₂Cl₂ / 1 h

With aluminum amalgam; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jo00025a034

upstream raw materials:

methyl α-L-evernitroside

methyl 4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoyl)-3-O-(2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-α-L-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside

methyl 4-O-(4-benzyloxy-3,5-dichloro-2-methoxy-6-methylbenzoyl)-3-O-(2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-α-L-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside

2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-1-O-(p-nitrobenzoyl)-α-L-arabino-hexopyranose

Downstream raw materials:

methyl 3-O-(3-acetamido-2,3,6-trideoxy-3-C-methyl-4-O-methyl-α-L-arabino-hexopyranosyl)-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoyl)-2,6-dideoxy-α-D-arabino-hexopyranoside

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