methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate
• CAS No.: 392712-29-7
• Molecular Formula: C₂₅H₃₀N₂O₁₁
• Molecular Weight: 534.52

Synonyms:methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

Chemical Property of methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

Chemical Property:

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Technology Process of methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

There total 4 articles about methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate 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: 89.0%

benzoic acid anhydride (93-97-0) + 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester (139110-70-6) → methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate (392712-29-7)

Guidance literature:

With dmap; In pyridine; at 20 ℃;

DOI:10.1081/CAR-100105710

Reference yield: 80.0%

benzoyl chloride (98-88-4) + 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester (139110-70-6) → methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate (392712-29-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1039/c6md00519e

Reference yield: 52.0%

(1S,5S,7R,8R)-8-Acetylamino-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester (392712-45-7) → methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate (392712-29-7) + methyl 5-acetamido-7,8,9-tri-O-acetyl-2-azido-4-benzamido-2,3,4,5-tetradeoxy-D-glycero-β-D-galacto-2-nonulopyranosonate

Guidance literature:

With trimethylsilylazide; In tetrahydrofuran; for 16h; Heating;

DOI:10.1081/CAR-100105710

upstream raw materials:

benzoic acid anhydride

5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester

(1S,5S,7R,8R)-8-Acetylamino-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

(1R,5R,7R,8R,9S)-8-Acetylamino-9-bromo-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

Downstream raw materials:

(1R,5R,7R,8R,9S)-8-Acetylamino-9-bromo-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

(1S,5S,7R,8R)-8-Acetylamino-3-phenyl-7-((1S,2R)-1,2,3-triacetoxy-propyl)-4,6-dioxa-2-aza-bicyclo[3.3.1]non-2-ene-5-carboxylic acid methyl ester

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