3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester

Base Information

• Chemical Name: 3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester
• CAS No.: 648431-76-9
• Molecular Formula: C₁₇H₂₁NO₇
• Molecular Weight: 351.356

Synonyms:3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester

Chemical Property of 3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester

Chemical Property:

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Technology Process of 3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester

There total 2 articles about 3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl 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:

3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester (260551-09-5) → 3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester (648431-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: AcOH; H₂ / Pd/C / 20 °C

2: 310 mg / p-TsOH*H₂O / dimethylformamide / 2 h / 40 °C

With hydrogen; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00366-3

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + (2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid methyl ester → 3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester (648431-76-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

DOI:10.1016/S0968-0896(03)00366-3

Reference yield: 61.0%

ethyl 2,3-di-O-benzoyl-4,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside (260969-99-1) + 3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester (648431-76-9) → 2',3'-di-O-benzoyl-4',6'-dideoxy-α-L-lyxo-hexopyranosyl-(1->4)-3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester (648431-78-1)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃;

DOI:10.1016/S0968-0896(03)00366-3

upstream raw materials:

benzaldehyde dimethyl acetal

3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester

Downstream raw materials:

2',3'-di-O-benzoyl-4',6'-dideoxy-α-L-lyxo-hexopyranosyl-(1->4)-3-acetamido-2,6-anhydro-5,7-O-benzylidene-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester

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