N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol

Base Information

• Chemical Name: N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol
• CAS No.: 1416243-73-6
• Molecular Formula: C₂₀H₂₇F₃N₂O₅
• Molecular Weight: 432.44
• Mol file: 1416243-73-6.mol

Synonyms:N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol

Chemical Property of N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol

There total 2 articles about N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-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: 60.0%

6-(trifluoroacetamido)hexanoic acid (407-91-0) + 3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol (1199942-81-8) → N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol (1416243-73-6)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 18h;

DOI:10.1021/bc3004974

Reference yield:

N-Benzyl-3-benzyl-3,4,5-trans,trans-trihydroxypiperidine → N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol (1416243-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 18 h / 20 °C

2: dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 18 h / 0 - 20 °C

With 10 wt% Pd(OH)2 on carbon; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In ethanol; dichloromethane;

DOI:10.1021/bc3004974

Reference yield: 37.0%

2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl trichloroacetimidate (1190224-19-1) + N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol (1416243-73-6) → N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-2,4-bis-O-(2,3,4,6-tetra-O-methoxyacetyl-α-D-manno-pyranosyl)-1,5-dideoxy-1,5-iminoxylitol (1416243-80-5)

Guidance literature:

2,3,4,6-tetra-O-methoxyacetyl-α-D-mannopyranosyl trichloroacetimidate; N-(6-trifluoroacetamidohexanoyl)-3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol; In dichloromethane; for 0.25h; Inert atmosphere; Molecular sieve; Reflux;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1021/bc3004974

upstream raw materials:

6-(trifluoroacetamido)hexanoic acid

3-O-benzyl-1,5-dideoxy-1,5-iminoxylitol

Downstream raw materials:

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