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

Base Information

Chemical Name:4,6-O-[(R)-benzylidene]-N-[(2R,3S)-3-benzyloxy-2-fluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine
CAS No.:191157-48-9
Molecular Formula:C₆₂H₁₀₀FNO₁₀
Molecular Weight:1038.48
Hs Code.:

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

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

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

There total 9 articles about 4,6-O-[(R)-benzylidene]-N-[(2R,3S)-3-benzyloxy-2-fluorotetradecanoyl]-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: 67.0%

: 87357-76-4
(R)-3-(dodecanoyloxy)tetradecanoic acid

: 191157-44-5
4,6-O-[(R)-benzylidene]-N-[(2R,3S)-3-benzyloxy-2-fluorotetradecanoyl]-β-D-glucopyranosylamine

: 191157-48-9
4,6-O-[(R)-benzylidene]-N-[(2R,3S)-3-benzyloxy-2-fluorotetradecanoyl]-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:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 191157-48-9
4,6-O-[(R)-benzylidene]-N-[(2R,3S)-3-benzyloxy-2-fluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 16 h / 25 °C

2: 60 percent / NaOH / ethanol; H₂O / 2 h / 50 °C

3: oxalyl chloride / CH₂Cl₂ / 1 h / 24 °C

4: 37.8 percent / triethylamine / CH₂Cl₂ / 15 h / 0 - 24 °C

5: sodium methoxide / methanol / 0.5 h / 24 °C

6: 0.64 g / (+/-)-10-camphorsulfonic acid / dimethylformamide / 16 h / 24 °C

7: 67 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / diethyl ether / 1 h / 25 °C

With dmap; sodium hydroxide; oxalyl dichloride; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; sodium methylate; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Etherification / 2: Hydrolysis / 3: Chlorination / 4: Acylation / 5: Deacetylation / 6: Cyclization / 7: Esterification;
DOI:10.1246/bcsj.70.1149

Reference yield:

: (+/-)-methyl threo-2-fluoro-3-hydroxytetradecanoate

: 191157-48-9
4,6-O-[(R)-benzylidene]-N-[(2R,3S)-3-benzyloxy-2-fluorotetradecanoyl]-2-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 16 h / 25 °C

2: 60 percent / NaOH / ethanol; H₂O / 2 h / 50 °C

3: oxalyl chloride / CH₂Cl₂ / 1 h / 24 °C

4: 37.8 percent / triethylamine / CH₂Cl₂ / 15 h / 0 - 24 °C

5: sodium methoxide / methanol / 0.5 h / 24 °C

6: 0.64 g / (+/-)-10-camphorsulfonic acid / dimethylformamide / 16 h / 24 °C

7: 67 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / diethyl ether / 1 h / 25 °C

With dmap; sodium hydroxide; oxalyl dichloride; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; sodium methylate; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Etherification / 2: Hydrolysis / 3: Chlorination / 4: Acylation / 5: Deacetylation / 6: Cyclization / 7: Esterification;
DOI:10.1246/bcsj.70.1149