2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose

Base Information

• Chemical Name: 2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose
• CAS No.: 257925-76-1
• Molecular Formula: C₂₀H₂₃NO₅Se
• Molecular Weight: 436.366
• Mol file: 257925-76-1.mol

Synonyms:2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose

Chemical Property of 2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose

There total 8 articles about 2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose 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: 95.0%

bis(trichloromethyl) carbonate (32315-10-9) + 2-O-benzoyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose (257925-77-2) → 2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose (257925-76-1)

Guidance literature:

With pyridine; In dichloromethane; at -78 - 20 ℃; for 1h;

DOI:10.1071/CH99030

Reference yield:

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside (257925-66-9) → 2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose (257925-76-1)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂; AcCl / 10 percent Pd-C / ethyl acetate; methanol / 6 h

2: pyridine / 2.5 h / 0 - 20 °C

3: 77 percent / HBr / acetic acid / 48 h / 20 °C

4: 76 percent / NaBH₄; Se / ethanol; dimethylformamide

5: 83 percent / NaOMe / methanol / 0 °C

6: 87 percent / butan-1-ol / 16 h / 100 °C

7: 84 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / -50 - -20 °C

8: 95 percent / pyridine / CH₂Cl₂ / 1 h / -78 - 20 °C

With pyridine; dmap; selenium; sodium tetrahydroborate; hydrogen bromide; hydrogen; sodium methylate; triethylamine; acetyl chloride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; butan-1-ol; 1: Hydrogenolysis / 2: Esterification / 3: Substitution / 4: Cyclization / 5: Epoxidation / 6: Addition / 7: Esterification / 8: Cyclization;

DOI:10.1071/CH99030

Reference yield:

2,3-di-O-acetyl-4,6-di-O-methylsulfonyl-α-D-glucopyranosyl bromide (178319-23-8) → 2-O-benzoyl-3,4-O,N-carbonyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose (257925-76-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / NaBH₄; Se / ethanol; dimethylformamide

2: 83 percent / NaOMe / methanol / 0 °C

3: 87 percent / butan-1-ol / 16 h / 100 °C

4: 84 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / -50 - -20 °C

5: 95 percent / pyridine / CH₂Cl₂ / 1 h / -78 - 20 °C

With pyridine; dmap; selenium; sodium tetrahydroborate; sodium methylate; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol; 1: Cyclization / 2: Epoxidation / 3: Addition / 4: Esterification / 5: Cyclization;

DOI:10.1071/CH99030

upstream raw materials:

bis(trichloromethyl) carbonate

2-O-benzoyl-4-cyclohexylamino-1,6-episeleno-1,4,6-trideoxy-β-D-glucopyranose

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside

2,3-di-O-acetyl-4,6-di-O-methylsulfonyl-α-D-glucopyranosyl bromide