4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose

Base Information

• Chemical Name: 4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose
• CAS No.: 1415238-67-3
• Molecular Formula: C₂₅H₃₃F₂NO₁₂
• Molecular Weight: 577.533
• Mol file: 1415238-67-3.mol

Synonyms:4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose

Chemical Property of 4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose

There total 4 articles about 4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose 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: 99.0%

4-(hex-5-yneamide)-2-difluromethyl-1-phenoxyl-2,3,4,6,2′ ,3′ ,4′ ,6′-hepta-O-acetyl-1-phenoxyl-α-D-lactopyranose (1415238-68-4) → 4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose (1415238-67-3)

Guidance literature:

4-(hex-5-yneamide)-2-difluromethyl-1-phenoxyl-2,3,4,6,2′ ,3′ ,4′ ,6′-hepta-O-acetyl-1-phenoxyl-α-D-lactopyranose; With sodium methylate; In methanol; at 20 ℃; for 1h; Inert atmosphere;

In methanol; Inert atmosphere;

DOI:10.1021/ja309790w

Reference yield:

2-formyl-4-nitro 2,3,4,6,2′ ,3′,4′ ,6′-hepta-O-acetyl-1-phenoxyl-α-D-lactopyranose (1415238-58-2) → 4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose (1415238-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diethylamino-sulfur trifluoride / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / Inert atmosphere

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere

3.2: 48 h / 20 °C / Inert atmosphere

4.1: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere

4.2: amberlite IR-15 H+ resin / Inert atmosphere

With 4-methyl-morpholine; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; hydrogen; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja309790w

Reference yield:

2-difluromethyl-4-nitro 2,3,4,6,2′ ,3′ ,4′ ,6′-hepta-O-acetyl-1-phenoxyl-α-D-lactopyranose (1415238-59-3) → 4-(hex-5-yneamide)-2-difluromethyl 1-deoxy-1-phenoxyl-α-D-lactopyranose (1415238-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / Inert atmosphere

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere

2.2: 48 h / 20 °C / Inert atmosphere

3.1: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere

3.2: amberlite IR-15 H+ resin / Inert atmosphere

With 4-methyl-morpholine; palladium 10% on activated carbon; hydrogen; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja309790w

upstream raw materials:

2-formyl-4-nitro 2,3,4,6,2′ ,3′,4′ ,6′-hepta-O-acetyl-1-phenoxyl-α-D-lactopyranose

2-difluromethyl-4-nitro 2,3,4,6,2′ ,3′ ,4′ ,6′-hepta-O-acetyl-1-phenoxyl-α-D-lactopyranose

C₃₃H₄₁F₂NO₁₈

4-(hex-5-yneamide)-2-difluromethyl-1-phenoxyl-2,3,4,6,2′ ,3′ ,4′ ,6′-hepta-O-acetyl-1-phenoxyl-α-D-lactopyranose