3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Base Information

• Chemical Name: 3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS No.: 252210-06-3
• Molecular Formula: C₂₄H₃₁NO₁₁
• Molecular Weight: 509.51
• Mol file: 252210-06-3.mol

Synonyms:3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Chemical Property of 3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

There total 3 articles about 3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 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:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) → 3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (252210-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / TMSOTf / CH₂Cl₂ / 4 h / -30 - 0 °C

2: H₂ / DeGussa Pd/C / ethanol / 1.5 h

3: Et₃N / tetrahydrofuran / 16 h / 25 °C

With trimethylsilyl trifluoromethanesulfonate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 1: Condensation / 2: Reduction / 3: Condensation;

DOI:10.1021/ja991729e

Reference yield:

(3-azidopropyl) 2,3,4,6-tetra-O-acetate-α-D-mannopyranoside (252210-04-1) → 3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (252210-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / DeGussa Pd/C / ethanol / 1.5 h

2: Et₃N / tetrahydrofuran / 16 h / 25 °C

With hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; 1: Reduction / 2: Condensation;

DOI:10.1021/ja991729e

Reference yield:

benzoyl chloride (98-88-4) + (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(3-aminopropoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (252210-05-2) → 3-(benzylamido)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (252210-06-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 25 ℃; for 16h;

DOI:10.1021/ja991729e

upstream raw materials:

benzoyl chloride

(2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(3-aminopropoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

(3-azidopropyl) 2,3,4,6-tetra-O-acetate-α-D-mannopyranoside