4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Base Information

• Chemical Name: 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine
• CAS No.: 191157-46-7
• Molecular Formula: C₆₂H₉₉F₂NO₁₀
• Molecular Weight: 1056.47

Synonyms:4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Chemical Property of 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

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Technology Process of 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

There total 2 articles about 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine 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%

(R)-3-(dodecanoyloxy)tetradecanoic acid (87357-76-4) + 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-β-D-glucopyranosylamine → 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine (191157-46-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In diethyl ether; at 25 ℃; for 1h;

DOI:10.1246/bcsj.70.1149

Reference yield: 33.0%

(R)-3-(dodecanoyloxy)tetradecanoic acid (87357-76-4) + 4,6-O-[(R)-benzylidene]-N-(3-benzyloxy-2,2-difluorotetradecanoyl)-β-D-glucopyranosylamine (191157-42-3) → 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine (191157-46-7) + 4,6-O-[(R)-benzylidene]-N-[(R)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In diethyl ether; at 25 ℃; for 1h;

DOI:10.1246/bcsj.70.1149

Reference yield: 96.0%

chlorophosphoric acid diphenyl ester (2524-64-3) + 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine (191157-46-7) → 4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-3-O-diphenylphosphono-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine (191157-50-3)

Guidance literature:

With dmap; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1246/bcsj.70.1149

upstream raw materials:

(R)-3-(dodecanoyloxy)tetradecanoic acid

4,6-O-[(R)-benzylidene]-N-(3-benzyloxy-2,2-difluorotetradecanoyl)-β-D-glucopyranosylamine

Downstream raw materials:

4,6-O-[(R)-benzylidene]-N-[(S)-3-benzyloxy-2,2-difluorotetradecanoyl]-3-O-diphenylphosphono-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

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