methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate
• CAS No.: 1304780-03-7
• Molecular Formula: C₃₁H₄₇N₃O₁₀S
• Molecular Weight: 653.794
• Mol file: 1304780-03-7.mol

Synonyms:methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate

Chemical Property of methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate

There total 7 articles about methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-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: 100.0%

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate (909103-59-9) + 4-toluenesulfonyl azide (941-55-9) + diisopropylamine (108-18-9) → methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate (1304780-03-7)

Guidance literature:

With copper(l) iodide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.02.010

Reference yield:

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate (25875-99-4,79026-38-3) → methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate (1304780-03-7)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide

2: 15-crown-5; sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

3: copper(l) iodide / dichloromethane / 1 h / 20 °C / Inert atmosphere

With copper(l) iodide; 15-crown-5; sodium hydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.02.010

Reference yield:

N-acetylneuraminic acid methyl ester (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2) → methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate (1304780-03-7)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine

2: triphenylphosphine hydrobromide / acetonitrile / 4 h / 60 °C

3: methanol; sodium methylate

4: toluene-4-sulfonic acid / N,N-dimethyl-formamide

5: 15-crown-5; sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

6: copper(l) iodide / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; methanol; copper(l) iodide; 15-crown-5; sodium methylate; triphenylphosphine hydrobromide; sodium hydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Zemplen deacetylation;

DOI:10.1016/j.bmc.2011.02.010

upstream raw materials:

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate

4-toluenesulfonyl azide

diisopropylamine

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

Downstream raw materials:

5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(diisopropylamino)-3-(tosylimino)propoxy]-D-glycero-D-galacto-non-2-enonic acid