N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide

Base Information

• Chemical Name: N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide
• CAS No.: 271588-08-0
• Molecular Formula: C₁₉H₂₈Cl₂N₂O₈
• Molecular Weight: 483.346

Synonyms:N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide

Chemical Property of N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide

Chemical Property:

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Technology Process of N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide

There total 3 articles about N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide 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:

endo-4-O-Cyclohexylcarbamoyl-6-O-formyl-2,3-O-(2,2,2-trichloroethylidene)-β-D-gulopyranosyl azide (271588-03-5) → N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide (271588-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / Et₃N / methanol / 0.17 h / Heating

2: Bu₃SnH; AIBN / toluene / 3 h / 50 °C

3: pyridine / 12 h / 20 °C

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In methanol; toluene; 1: Substitution / 2: Reduction / 3: Acetylation;

DOI:10.1055/s-2000-6250

Reference yield:

endo-4-O-Cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-β-D-gulopyranosyl azide (271588-02-4) → N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide (271588-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₃SnH; AIBN / toluene / 3 h / 50 °C

2: pyridine / 12 h / 20 °C

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; 1: Reduction / 2: Acetylation;

DOI:10.1055/s-2000-6250

Reference yield:

acetic anhydride (108-24-7) + Cyclohexyl-carbamic acid (2S,3aR,4R,6R,7S,7aR)-4-amino-2-dichloromethyl-6-hydroxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester → N-[6-O-Acetyl-4-O-cyclohexylcarbamoyl-2,3-O-(2,2-dichloroethylidene)-β-D-gulopyranosyl]acetamide (271588-08-0)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1055/s-2000-6250

upstream raw materials:

acetic anhydride

endo-4-O-Cyclohexylcarbamoyl-6-O-formyl-2,3-O-(2,2,2-trichloroethylidene)-β-D-gulopyranosyl azide

endo-4-O-Cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-β-D-gulopyranosyl azide

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