3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Base Information

Chemical Name:3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine
CAS No.:177085-93-7
Molecular Formula:C₆₀H₁₀₀NO₁₃P
Molecular Weight:1074.43
Hs Code.:

Synonyms:3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

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Chemical Property of 3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

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Technology Process of 3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

There total 16 articles about 3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-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: 77.0%

: 177085-92-6
N-[(R)-3-(benzyloxy)tetradecanoyl]-3-O-diphenylphosphono-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

: 177085-93-7
3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 25 ℃; for 3h;
DOI:10.1246/cl.1996.735

Reference yield:

: 41355-50-4,51642-81-0,58484-22-3,70128-27-7,70145-20-9,94482-21-0,98300-76-6
2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine

: 177085-93-7
3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 7 steps

1: 84 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

2: sodium methoxide / methanol / 0.5 h / 25 °C

3: 570 mg / pyridinium p-toluenesulfonate / dimethylformamide / 3 h / 25 °C

4: 67 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / diethyl ether / 1 h / 25 °C

5: 94 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 25 °C

6: 76 percent / acetic acid; H₂O / 5 h / 60 °C

7: 77 percent / hydrogen / Pd on carbon / tetrahydrofuran / 3 h / 25 °C

With dmap; water; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Deacetylation / 3: Cyclization / 4: Esterification / 5: phosphorylation / 6: Hydrolysis / 7: Hydrogenolysis;
DOI:10.1246/bcsj.70.1149

Reference yield:

: (R)-3-Benzyloxy-tetradecanoic acid ((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-amide

: 177085-93-7
3-O-diphenylphosphono-N-[(R)-3-(hydroxy)tetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 5 steps

1: 570 mg / pyridinium p-toluenesulfonate / dimethylformamide / 3 h / 25 °C

2: 67 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / diethyl ether / 1 h / 25 °C

3: 94 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 25 °C

4: 76 percent / acetic acid; H₂O / 5 h / 60 °C

5: 77 percent / hydrogen / Pd on carbon / tetrahydrofuran / 3 h / 25 °C

With dmap; water; hydrogen; pyridinium p-toluenesulfonate; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Esterification / 3: phosphorylation / 4: Hydrolysis / 5: Hydrogenolysis;
DOI:10.1246/bcsj.70.1149