N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol

Base Information

• Chemical Name: N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol
• CAS No.: 1199942-83-0
• Molecular Formula: C₅₀H₆₈F₃NO₃₀
• Molecular Weight: 1220.07
• Mol file: 1199942-83-0.mol

Synonyms:N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol

Chemical Property of N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol

There total 12 articles about N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol 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: 47.0%

N-trifluoroacetamido-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol (1199942-82-9) + 2,3,4,6-tetra-O-methoxyacetyl-1-O-trichloroacetimidoyl-α-D-mannopyranose → N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol (1199942-83-0)

Guidance literature:

N-trifluoroacetamido-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol; 2,3,4,6-tetra-O-methoxyacetyl-1-O-trichloroacetimidoyl-α-D-mannopyranose; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 2h;

Reference yield: 47.0%

N-trifluoroacetamido-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol (1199942-82-9) + 2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl trichloroacetimidate (1190224-19-1) → N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol (1199942-83-0)

Guidance literature:

N-trifluoroacetamido-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol; In dichloromethane; for 0.5h; Molecular sieve; Inert atmosphere;

2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl trichloroacetimidate; In dichloromethane; for 1h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1002/cmdc.201100291

Reference yield:

N-Benzyl-3-benzyl-3,4,5-trans,trans-trihydroxypiperidine → N-trifluoroacetamido-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl)-1,5-dideoxy-1,5-iminoxylitol (1199942-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen / 20% palladium hydroxide-activated charcoal / ethanol / 20 h / 20 °C

2.1: pyridine / dichloromethane / 18 h / 20 °C

3.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 2 h / 20 °C

With pyridine; hydrogen; 20% palladium hydroxide-activated charcoal; In ethanol; dichloromethane;

upstream raw materials:

benzyl bromide

D-Mannose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose