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

Base Information

• Chemical Name: 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
• CAS No.: 137333-02-9
• Molecular Formula: C₂₄H₃₃Cl₂NO₁₁
• Molecular Weight: 582.432

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 3 articles about 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 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: 85.0%

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) → 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 (137333-02-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In various solvent(s); for 1h;

DOI:10.1021/jo00025a034

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) → 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 (137333-02-9)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; hydrogen; palladium on activated charcoal; In 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) → 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 (137333-02-9)

Guidance literature:

Multi-step reaction with 2 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

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jo00025a034

upstream raw materials:

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

methyl α-L-evernitroside

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-amino-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

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

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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