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[ CAS No. 1005500-75-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1005500-75-3
Chemical Structure| 1005500-75-3
Chemical Structure| 1005500-75-3
Structure of 1005500-75-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1005500-75-3 ]

CAS No. :1005500-75-3 MDL No. :MFCD30861485
Formula : C10H11NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :VRNLIJIYOKNEOP-UHFFFAOYSA-N
M.W :209.26 Pubchem ID :51357211
Synonyms :

Calculated chemistry of [ 1005500-75-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.17
TPSA : 45.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 1.5
Log Po/w (SILICOS-IT) : 0.89
Consensus Log Po/w : 1.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.721 mg/ml ; 0.00344 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.852 mg/ml ; 0.00407 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.628 mg/ml ; 0.003 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.32

Safety of [ 1005500-75-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1005500-75-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1005500-75-3 ]

[ 1005500-75-3 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 1885-38-7 ]
  • [ 1005500-75-3 ]
  • (E)-N,N'-(6-styrylpyridine-2,4-diyl)bis(N,4-dimethylbenzenesulfonamide) [ No CAS ]
  • 2
  • [ 1005500-75-3 ]
  • [ 65-85-0 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique;
99% In dichloromethane at 25℃; for 1.5h;
99% In dichloromethane at 20℃; for 1.5h; 16 Example 16 In a clean 25 mL reaction tubeN-methyl-N-ethynyl-p-toluenesulfonamide (0.20 mmol) was added,Benzoic acid (0.2 mmol),Adding appropriate amount of dichloromethane as solvent,At room temperature for 1.5 hours,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
99% In dichloromethane at 20℃;
With silver(l) oxide In 1,4-dioxane at 100℃; for 5h; Inert atmosphere; Schlenk technique;
In dichloromethane at 20℃; for 2h;

  • 3
  • [ 64-18-6 ]
  • [ 1005500-75-3 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 25℃; for 0.166667h;
99% In dichloromethane at 10℃; for 0.166667h; 1 Example 1 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.20 mmol) was added,Formic acid (2 mmol),Adding appropriate amount of dichloromethane as solvent,At 10 degrees Celsius,Reaction for 10 minutes,TLC spot plate detection,After completion of the reaction the solvent was concentrated and subjected to column chromatography to give the pure product as a white solid,Yield 99%.
  • 4
  • [ 1005500-75-3 ]
  • [ 828-51-3 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl adamantane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 0℃; for 4h; 2 Example 2 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.20 mmol) was added, 1-adamantanecarboxylic acid (0.3 mmol),Adding appropriate amount of dichloromethane as solvent,At 0 degrees Celsius reaction 4 hours,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
98% In dichloromethane at 25℃; for 3h;
  • 5
  • [ 1005500-75-3 ]
  • [ 74-11-3 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl 4-chlorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃; for 6h; 3 Example 3 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.30 mmol) was added, p-chlorobenzoic acid (0.2 mmol),Adding appropriate amount of dichloromethane as solvent,At room temperature for 6 hours,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
99% In dichloromethane at 20℃;
98% In dichloromethane at 25℃; for 4h;
In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 1h; Schlenk technique; Inert atmosphere;

  • 6
  • [ 88-14-2 ]
  • [ 1005500-75-3 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl furan-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃;
98% In dichloromethane at 25℃; for 0.5h;
98% In dichloromethane at 20℃; for 0.5h; 4 Example 4 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide(0.20 mmol) was added, 2-furoic acid (0.2 mmol),Adding appropriate amount of dichloromethane as solvent,At room temperature for 30 minutes,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 98%.
  • 7
  • [ 50890-83-0 ]
  • [ 1005500-75-3 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl 1-methyl-1H-indazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In chloroform; at 20℃; for 5h; In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (2.0 mmol) was added, <strong>[50890-83-0]1-methylindazole-3-carboxylic acid</strong> (0.2 mmol)Add appropriate amount of chloroform as solvent,At room temperature for 5 hours,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
  • 8
  • [ 5381-25-9 ]
  • [ 1005500-75-3 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl benzo[b]thiophene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane; at 40℃; for 1h; In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (1.0 mmol) was added, <strong>[5381-25-9]1-<strong>[5381-25-9]benzothiophene-3-carboxylic acid</strong></strong> (0.2 mmol)Adding appropriate amount of dichloromethane as solvent,At 40 degrees Celsius for 1 hour,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 100%.
  • 9
  • [ 1005500-75-3 ]
  • [ 637-44-5 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl 3-phenylpropiolate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 25℃; for 0.133333h;
99% In dichloromethane at 0℃; for 0.166667h; 8 Example 8 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.80 mmol) was added, phenylpropiolic acid (0.2 mmol),Adding appropriate amount of dichloromethane as solvent,Reaction at 0 ° C for 10 minutes,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
  • 10
  • [ 1005500-75-3 ]
  • [ 102410-65-1 ]
  • C33H30N2O6S [ No CAS ]
  • 11
  • [ 1005500-75-3 ]
  • [ 1145-80-8 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl ((benzyloxy)carbonyl)-L-serinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 25℃; for 0.583333h;
99% In dichloromethane at 30℃; for 0.5h; 9 Example 9 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.20 mmol) was added, N-benzyloxycarbonyl-L-serine (0.2 mmol)Adding appropriate amount of dichloromethane as solvent,At 30 degrees Celsius for 30 minutes,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,solid,Yield 99%.
  • 12
  • [ 1005500-75-3 ]
  • [ 73731-37-0 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-threoninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 25℃; for 0.75h;
99% In dichloromethane at 20℃; for 0.666667h; 10 Example 10 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.20 mmol) was added,Fmoc-L-threonine (0.2 mmol),Adding appropriate amount of dichloromethane as solvent,At room temperature for 40 minutes,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
  • 13
  • [ 1005500-75-3 ]
  • [ 7432-21-5 ]
  • N-benzyloxycarbonyl-L-tryptophan 1-(N-methyl-p-toluenesulfonamido)ethenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃; for 0.5h; 11 Example 11 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.20 mmol) was added, N-benzyloxycarbonyl-L-tryptophan (0.24 mmol)Adding appropriate amount of dichloromethane as solvent,At room temperature for 30 minutes,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
99% In dichloromethane at 20℃;
In dichloromethane at 35℃;
  • 14
  • [ 1005500-75-3 ]
  • [ 81-23-2 ]
  • [ 100-52-7 ]
  • [ 62-53-3 ]
  • (4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N-((R)-3-((N,4-dimethylphenyl)sulfonamido)-3-oxo-1-phenylpropyl)-N-phenylpentanamide [ No CAS ]
  • 15
  • [ 57476-50-3 ]
  • [ 1005500-75-3 ]
  • [ 62-53-3 ]
  • [ 65-85-0 ]
  • tert-butyl-3-(3-((N,4-dimethylphenyl)sulfonamido)-3-oxo-1-(N-phenylbenzamido)propyl)-1H-indole-1-carboxylate [ No CAS ]
  • 16
  • [ 1005500-75-3 ]
  • [ 621-82-9 ]
  • 1-(N-methyl-p-toluenesulfonamido)ethenyl 3-phenylprop-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In 1,2-dichloro-ethane at 50℃; for 1h; 7 Example 7 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.80 mmol) was added,Cinnamic acid (0.2 mmol),Adding appropriate amount of 1,2-dichloroethane as solvent,At 50 ° C for 1 hour,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
  • 17
  • [ 1005500-75-3 ]
  • [ 13734-34-4 ]
  • C24H30N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃; for 0.5h; 12 Example 12 In a clean 25 mL reaction tube N-methyl-N-ethynyl-p-toluenesulfonamide (0.20 mmol) was added, N-(tert-butoxycarbonyl)-L-phenylalanine (0.2 mmol)Adding appropriate amount of dichloromethane as solvent,At room temperature for 30 minutes,TLC spot plate detection,After completion of the reaction, the solvent was concentrated and subjected to column chromatography to give pure product,White solid,Yield 99%.
99% In dichloromethane at 20℃;
  • 18
  • [ 57476-50-3 ]
  • [ 1005500-75-3 ]
  • [ 62-23-7 ]
  • 3-(3-((N,4-dimethylphenyl)sulfonamido)-1-((4-nitrobenzoyl)oxy)-3-oxopropyl)-1H-indole-1-carboxylate [ No CAS ]
  • 19
  • [ 75-35-4 ]
  • [ 640-61-9 ]
  • [ 1005500-75-3 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide; In N,N-dimethyl-formamide; at 70℃; for 24h;Schlenk technique; Add 0.2 mmol of N-methyl-p-toluenesulfonamide and a stirrer to a clean Schlenk reaction tube.Then, 1.0 mL of DMF solvent was added by syringe, and 1.0 mmol of NaOH was added to the reaction tube.Finally, 0.6 mmol of 1,1-dichloroethylene was added with a micro syringe, and the bottle was stoppered with a soft rubber stopper, and reacted at 70 C for 24 hours.TLC dot plate detection; after the reaction is completed, the reaction solution is added with ice water and extracted with ethyl acetate three times.The organic layer is concentrated and separated by column chromatography to obtain pure N-methyl-N-ethynyl p-toluenesulfonamide.White solid, yield 93%.
  • 20
  • [ 1005500-75-3 ]
  • [ 640-61-9 ]
  • (Z)-N,N′-(ethene-1,2-diyl)bis(N,4-dimethylbenzenesulfonamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; 1 Example 1 Add 0.1 mmol of cesium carbonate to the clean Schlenk reaction tube, N-methyl-N-ethynyl p-toluenesulfonamide(0.2 mmol), N-methyl-p-toluenesulfonamide (0.4 mmol) and a stirrer, then add 1 mL of dimethyl sulfoxide, and finally stopper the bottle with a soft rubber stopper, and react at room temperature for 24 hours, TLC dot plate After the reaction is completed, after the reaction is completed, the pure product is obtained by column chromatography to give a white solid, yield 99%.
99% With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; stereoselective reaction;
  • 21
  • [ 1005500-75-3 ]
  • [ 6333-79-5 ]
  • (Z)-4-chloro-N-(2-((N,4-dimethylphenyl)sulfonamido)vinyl)-N-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; 3 Example 3 Add 0.1 mmol of cesium carbonate to the clean Schlenk reaction tube, N-methyl-N-ethynyl p-toluenesulfonamide(0.2 mmol), N-methyl-p-chlorobenzenesulfonamide (0.4 mmol) and a stirrer, then add 1 mL of dimethyl sulfoxide, and finally stopper the bottle with a soft rubber stopper, and react at room temperature for 24 hours, TLC point Plate detection; after the reaction is completed, after the reaction is completed, the pure product is obtained by column chromatography to give a white solid, yield 94%.
94% With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; stereoselective reaction;
  • 22
  • [ 497-25-6 ]
  • [ 1005500-75-3 ]
  • (Z)-N,4-dimethyl-N-(2-(2-oxooxazolidin-3-yl)vinyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With caesium carbonate In dimethyl sulfoxide at 20℃; for 32h; Schlenk technique; 4 Example 4 Add 0.1 mmol of cesium carbonate to the clean Schlenk reaction tube, N-methyl-N-ethynyl p-toluenesulfonamide(0.2 mmol), 2-oxazolidinone (0.4 mmol) and a stirrer, then add 1 mL of dimethyl sulfoxide, and finally stopper the bottle with a soft rubber stopper, react at room temperature for 32 hours, and detect by TLC dot plate; After completion of the reaction, after completion of the reaction, the product was isolated by column chromatography to yield white solid, yield 76%.
76% With caesium carbonate In dimethyl sulfoxide at 20℃; for 32h; Schlenk technique; stereoselective reaction;
  • 23
  • [ 120-72-9 ]
  • [ 1005500-75-3 ]
  • (Z)-N-(2-(1H-indol-1-yl)vinyl)-N,4-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With caesium carbonate In dimethyl sulfoxide at 20℃; for 7h; Schlenk technique; stereoselective reaction;
82% With caesium carbonate In dimethyl sulfoxide at 20℃; for 6h; Schlenk technique; 5 Example 5 Add 0.1 mmol of cesium carbonate to the clean Schlenk reaction tube, N-methyl-N-ethynyl p-toluenesulfonamide(0.2mmol), indole(0.4mmol) and a stir bar,Then add 1mL of dimethyl sulfoxide,Finally, plug the bottle with a soft rubber plug.React at room temperature for 6 hours,TLC dot plate inspection;After the reaction is completed, after the reaction is completed, the pure product is obtained by column chromatography., white solid, yield 82%.
  • 24
  • [ 1005500-75-3 ]
  • [ 4559-70-0 ]
  • (Z)-N-(2-(diphenylphosphoryl)vinyl)-N,4-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetrabutyl ammonium fluoride; caesium carbonate In acetonitrile at 20℃; Schlenk technique; 6 Example 6 Add 0.3 mmol of cesium carbonate to the clean Schlenk reaction tube, N-methyl-N-ethynyl p-toluenesulfonamide(0.1 mmol), diphenylphosphine oxide (0.3 mmol), and tetrabutylammonium fluoride (0.02 mmol) and a stirrer, then 1 mL of acetonitrile was added, and finally the stopper was stoppered with a soft rubber stopper and reacted at room temperature. HLC, dot plate detection; after the reaction is completed, after the reaction is completed, the pure product is obtained by column chromatography, white solid, yield 83%
83% With tetrabutyl ammonium fluoride; caesium carbonate In acetonitrile at 20℃; for 7h; Schlenk technique; stereoselective reaction;
  • 25
  • [ 1005500-75-3 ]
  • [ 762-04-9 ]
  • diethyl (Z)-(2-((N,4-dimethylphenyl)sulfonamido)vinyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; 8 Example 8 Add 0.2 mmol of cesium carbonate to the clean Schlenk reaction tube, N-methyl-N-ethynyl p-toluenesulfonamide(0.2 mmol), diethyl phosphite (0.1 mmol) and a stirrer, then 1 mL of dimethyl sulfoxide was added, and finally the bottle was stoppered with a soft rubber stopper, and reacted at room temperature for 24 hours, and detected by TLC dot plate; After completion, after completion of the reaction, separation was carried out by column chromatography to give a pure product as a colorless oily liquid, yield 91%.
83% With caesium carbonate In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; stereoselective reaction;
  • 26
  • [ 1005500-75-3 ]
  • [ 829-85-6 ]
  • (Z)-N-(2-(diphenylphosphanyl)vinyl)-N,4-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.166667h; Schlenk technique; Inert atmosphere; 9 Example 9 Add 0.1 mmol of cesium carbonate to the clean Schlenk reaction tube, N-methyl-N-ethynyl p-toluenesulfonamide(0.2 mmol), diphenylphosphine (0.24 mmol) and a stir bar, then stopper the bottle with a soft rubber stopper, a pipe connected to a nitrogen-filled balloon, and three times the Schlenk reaction tube, then add 1 mL of dimethylsulfoxide . Yafeng, reacted at room temperature for 10 minutes, TLC dot plate detection; after the reaction is completed, the pure product is obtained by column chromatography, colorless oily liquid, yield 80%.
80% With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; stereoselective reaction;
  • 27
  • [ 1005500-75-3 ]
  • [ 10504-92-4 ]
  • (Z)-N-(2-((N,4-dimethylphenyl)sulfonamido)vinyl)-4-methyl-N-(4-methylbenzyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With caesium carbonate In dimethyl sulfoxide at 20℃; for 32h; Schlenk technique; 2 Example 2 0.1 mmol of cesium carbonate, N-methyl-N-ethynyl p-toluenesulfonamide (0.2 mmol), N-4-methylbenzyl p-toluenesulfonamide (0.4 mmol) were added to the clean Schlenk reaction tube along with stirring, then 1mL of dimethyl sulfoxide was added, finally, the bottle mouth was stoppered with a soft rubber stopper, and reacted at room temperature for 32 hours, and monitored by TLC point board ; after completion of the reaction, the product was isolated by column chromatography to give a white solid (yield: 77%).
70% With caesium carbonate In dimethyl sulfoxide at 20℃; for 32h; Schlenk technique; stereoselective reaction;
  • 28
  • [ 1005500-75-3 ]
  • [ 40473-50-5 ]
  • [ 81-23-2 ]
  • 2-(3-((N,4-dimethylphenyl)sulfonamido)-3-oxo-1-phenylpropyl)phenyl (4R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate [ No CAS ]
  • 29
  • [ 4617-33-8 ]
  • [ 1005500-75-3 ]
  • 1-(N,4-dimethylphenylsulfonylamino)vinyl 15-hydroxypentadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) chloride In dichloromethane at 20℃; for 24h; 3 Example 3, General procedure: Add alkyne amide (0.20mmol), 12-hydroxyalkanoic acid (0.2mmol) to a clean 4mL reaction tube, add 10mol% CuCl, add 2mL CH2Cl2 as solvent, react at room temperature for 24h, detect by TLC dot plate, solvent after reaction Concentrated and column chromatography to obtain a pure product. White solid, yield 91%
90% With copper(l) chloride In dichloromethane at 20℃;
  • 30
  • [ 1005500-75-3 ]
  • [ 141-22-0 ]
  • C28H45NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) cyanide In dichloromethane at 20℃; for 4h; 4 Example 4, General procedure: Add alkyne amide (0.20 mmol) and 12-hydroxyalkanoic acid (0.2 mmol) to a clean 4 mL reaction tube, add 10 mol% CuCN, add 2 mL CH2Cl2 as solvent, react at room temperature for 4 h, detect by TLC dot plate, and solvent after the reaction Concentrated and column chromatography to obtain a pure product. White solid, yield 91%.
  • 31
  • [ 1005500-75-3 ]
  • [ 765-01-5 ]
  • C20H29NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) chloride; In dichloromethane; at 20.0℃; for 4.0h; Add alkynamide(0.20 mmol), <strong>[765-01-5]10-hydroxy-2-decenoic acid</strong> (0.2 mmol) to a clean 25 mL reaction tube, add 10 mol% CuCl, add 4 mL of CH2Cl2 as a solvent, react at room temperature for 4 h, and detect by TLC dot plate. After the reaction, the solvent is concentrated and column chromatography is carried out to obtain a pure product. White solid, yield 91%.
  • 32
  • [ 1005500-75-3 ]
  • [ 934813-05-5 ]
  • C24H37NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) chloride In dichloromethane at 20℃; for 4h; 6 Example 6, Add alkynamide(0.20 mmol), (E)-14-hydroxy-2-14 enoic acid (0.2 mmol) to a clean 4 mL reaction tube, add 4 mL of CH2Cl2 as a solvent, add 10 mol% CuCl, and react at room temperature for 4 h, TLC Spot plate detection, after completion of the reaction, the solvent was concentrated and subjected to column chromatography to give a pure product as a white solid, yield 91%.
  • 33
  • [ 1005500-75-3 ]
  • 2-(3-(2-hydroxyethoxy)propyl)benzoic acid [ No CAS ]
  • 1-(N,4-dimethylphenylsulfonylamino)vinyl 2-(3-(2-hydroxyethoxy)propyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With copper(l) cyanide In dichloromethane at 20℃; for 4h; 7 Example 7, Add alkynamide(0.20 mmol), 2-(3-(2-hydroxyethoxy)propyl)benzoic acid (0.2 mmol) to a clean 4 mL reaction tube, add 4 mL of CH2Cl2 as a solvent, and add 10 mol% CuCN. The reaction was carried out for 4 h at room temperature, and the TLC plate was used for the detection. After the reaction, the solvent was concentrated and column chromatography was carried out to obtain a pure product. White solid, yield 100%.
92% In dichloromethane at 20℃;
  • 34
  • [ 1005500-75-3 ]
  • 2-(7-hydroxyheptyl)benzoic acid [ No CAS ]
  • C24H31NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With copper(l) chloride In dichloromethane at 20℃; for 4h; 8 Example 8, Add alkynamide(0.20mmol), 2-(7-hydroxyheptyl)benzoic acid (0.2mmol) to a clean 4mL reaction tube, add 4mL CH2Cl2 as solvent, add 10mol% CuCl, react at room temperature for 4h, TLC point plate After the end of the reaction, the solvent was concentrated and subjected to column chromatography to give a pure product as a white solid, yield 94%.
  • 35
  • [ 1005500-75-3 ]
  • 4-(11-hydroxyundec-1-yn-1-yl)benzoic acid [ No CAS ]
  • C28H35NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With copper(l) chloride In dichloromethane at 20℃; for 4h; 9 Example 9, Add alkynamide(0.20 mmol), 4-(11-hydroxyundec-1-yn-1-yl)benzoic acid (0.2 mmol) to a clean 4 mL reaction tube, add 4 mL of CH2Cl2 as solvent, and add 10 mol% CuCl. , reacted at room temperature for 4 h, detected by TLC dot plate, after the reaction is finished, the solvent is concentrated and column chromatography is carried out to obtain a pure product. White solid, yield 90%.
  • 36
  • [ 144649-40-1 ]
  • [ 1005500-75-3 ]
  • C31H44N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With copper(l) iodide In dichloromethane at 20℃; for 4h; 10 Example 10, Add alkynamide(0.20 mmol), (S)-2-(12-hydroxydodecanoylamino)-3-phenylpropionic acid (0.2 mmol) to a clean 4 mL reaction tube, and add 4 mL of CH2Cl2 as solvent. 10 mol% CuCl, reacted at room temperature for 4 h, detected by TLC dot plate, solvent concentration after column chromatography and column chromatography to obtain pure product, white solid, yield 89%.
  • 37
  • [ 1005500-75-3 ]
  • (S)-2-((S)-3-hydroxy-2-((9Z,12S)-12-hydroxyoctadec-9-enamido)propanamido)-4-methylpentanoic acid [ No CAS ]
  • C37H61N3O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With copper(l) iodide In dichloromethane at 20℃; for 4h; 11 Example 11, Add alkynamide(0.20 mmol), (S)-2-((S)-3-hydroxy-2-((9Z,12S)-12-hydroxyoctadec-9-enamido)propanamido)-4-methylpentanoic acid (0.2 mmol) to a clean reaction tube, adding 4 mL of CH2Cl2 as solvent, adding 10 mol% of CuI, reacting at room temperature for 4 h, detecting by TLC dot plate, solvent concentration after column chromatography and pure by column chromatography Product, white solid, yield 94%
  • 38
  • [ 1005500-75-3 ]
  • (S)-2-{2-[(S)-2-[(9Z,12S)-12-hydroxyoctadec-9-enamido]propanamido]acetamido}-4-methylpentanoic acid [ No CAS ]
  • C39H64N4O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With copper(l) chloride In dichloromethane at 20℃; for 4h; 12 Example 12, Add alkynamide(0.20 mmol) to a clean 4 mL reaction tube, (S)-2-{2-[(S)-2-[(9Z,12S)-12-hydroxyoctadec-9-enamido]propanamido]acetamido}-4-methylpentanoic acid (0.2mmol), adding 4mL CH2Cl2 as solvent, adding 10mol% CuCl, reacting at room temperature for 4h, detecting by TLC dot plate, solvent concentration after column reaction and column chromatography to obtain pure product. White solid, yield 93%
  • 39
  • [ 3710-42-7 ]
  • [ 1005500-75-3 ]
  • [ 539-87-7 ]
  • [ 16697-83-9 ]
  • 40
  • [ 3710-42-7 ]
  • [ 1005500-75-3 ]
  • 1-(N,4-dimethylphenylsulfonylamino)vinyl 7-hydroxyheptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) chloride; In dichloromethane; at 20℃; for 24h; General procedure: Add alkyne amide (0.22mmol), <strong>[3710-42-7]7-hydroxyheptanoic acid</strong> (0.2mmol) to a clean 4mL reaction flask, add 10mmol% CuCl catalyst, add 2mL CH2Cl2 as solvent, react at room temperature for 24h, detect by TLC plate, after the reaction is over. The solvent is concentrated and column chromatography to obtain a pure product.White solid, yield 92%.
  • 41
  • [ 1005500-75-3 ]
  • 12-hydroxydodecanamido-4-methylpentanoic acid [ No CAS ]
  • [ 16697-83-9 ]
  • C18H33NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: N-(methyl)-N-(p-toluenesulfonyl)ethynylamine; 12-hydroxydodecanamido-4-methylpentanoic acid With copper(l) chloride In dichloromethane at 20℃; for 2h; Stage #2: With toluene-4-sulfonic acid In dichloromethane for 4h; 20 Example 20, In a clean 25 mL round bottom flask, (12-hydroxydodecanamido-4-methylpentanoic acid (0.20 mmol) was added, 10moL CH2Cl2 was added as solvent, alkynamide (0.20 mmol) , 10 mol% CuCl were added and reacted at room temperature for 2 h, TLC dot plate detection, after the reaction was completed, 15 mol% of p-toluenesulfonic acid was added, and after reacting for 4 hours, the solvent was concentrated and subjected to column chromatography to obtain a pure product, a colorless liquid, yield: 92%.
  • 42
  • [ 1005500-75-3 ]
  • [(2S,11E,14S)-14-hydroxy-3-oxo-1-phenylicos-11-en-2-yl]carbamic acid [ No CAS ]
  • [ 16697-83-9 ]
  • C27H41NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: N-(methyl)-N-(p-toluenesulfonyl)ethynylamine; [(2S,11E,14S)-14-hydroxy-3-oxo-1-phenylicos-11-en-2-yl]carbamic acid With copper(l) chloride In dichloromethane at 20℃; for 2h; Stage #2: With toluene-4-sulfonic acid In dichloromethane for 4h; 21 Example 21, In a clean 25mL round bottom flask, [(2S,11E,14S)-14-hydroxy-3-oxo-1-phenylicos-11-en-2-yl]carbamic acid(0.20 mmol) was added, 10 mL of CH2CI2 was added as solvent, alkynamide (0.20mmol) and 10 mol% CuCl were added, after reacting at room temperature for 2 h, TLC dot plate was tested, and after the reaction was over, 15 mol% of p-toluenesulfonic acid was added, after 4 h of reaction, the solvent was concentrated and subjected to column chromatography to give a pure product as a colorless liquid, yield 85%.
  • 43
  • [ 505-95-3 ]
  • [ 1005500-75-3 ]
  • C22H35NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With copper(l) iodide In dichloromethane at 20℃; for 24h; 2 Example 2, General procedure: Add alkyne amide (0.22mmol), 12-hydroxyalkanoic acid (0.2mmol) to a clean 4mL reaction tube, add 10mol% CuI, add 2mL CH2Cl2 as solvent, react at room temperature for 24h, detect by TLC dot plate, solvent after reaction Concentrated and column chromatography to obtain a pure product. White solid, yield 93%.
87% With copper(l) chloride In dichloromethane at 20℃;
  • 44
  • [ 79-00-5 ]
  • [ 640-61-9 ]
  • [ 1005500-75-3 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydride In N,N-dimethyl-formamide at 80℃; for 1h; Schlenk technique; 1 Example 1 0.2 mmol of N-methyl-p-toluenesulfonamide and a stir bar were added to a clean Schlenk reaction tube, and then 1.0 mL of DMF solvent was added by a syringe.Add 1.4 mmol of NaH to the reaction tube.Finally, 1.0 mmol of 1,1,2-trichloroethane was added using a micro syringe.Then, the bottle mouth was stoppered with a soft rubber stopper, and reacted at 80 ° C for 1 hour, and the TLC dot plate was tested;After the reaction was completed, the reaction solution was added with ice water and extracted with ethyl acetate three times.The organic layer was concentrated and then purified by column chromatography to yield90% purified N-methyl-N-ethynyl p-toluenesulfonamide as a white solid.The structural formula of the product and its characterization data are as follows:
  • 45
  • [ 1005500-75-3 ]
  • [ 101023-70-5 ]
  • methyl 4-(5-((N,4-dimethylphenyl)sulfonamido)-3-(methyl-(tosyl)carbamoyl)-4-(p-tolyl)-1H-pyrrol-2-yl)benzoate [ No CAS ]
  • 46
  • [ 1005500-75-3 ]
  • [ 101023-70-5 ]
  • methyl 4-(5-((N,4-dimethylphenyl)sulfonamido)isoxazol-3-yl)benzoate [ No CAS ]
  • 47
  • [ 1005500-75-3 ]
  • C18H34O3 [ No CAS ]
  • C28H45NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) chloride In dichloromethane at 20℃;
  • 48
  • [ 764-89-6 ]
  • [ 1005500-75-3 ]
  • C18H27NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With copper(l) chloride In dichloromethane at 20℃;
76% In dichloromethane at 20℃;
  • 49
  • [ 1005500-75-3 ]
  • [ 1679-53-4 ]
  • C20H31NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With copper(l) chloride In dichloromethane at 20℃;
  • 50
  • [ 3669-80-5 ]
  • [ 1005500-75-3 ]
  • C21H33NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With copper(l) chloride In dichloromethane at 20℃;
  • 51
  • [ 1530-88-7 ]
  • [ 1005500-75-3 ]
  • N,4-dimethyl-N-(2-(pyrrolidin-1-yl)oxazol-5-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; 2,3-dichloropyridine N-oxide In neat (no solvent) at 60℃; for 3h;
  • 52
  • [ 1005500-75-3 ]
  • [ 15761-38-3 ]
  • 1-((N,4-dimethylphenyl)sulfonamido)vinyl(tert-butoxycarbonyl)-L-alaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃; for 2h; 1 Synthesis of compound 1a Add Boc-Ala-OH (0.2mmol), N-ethynyl-N-methylp-toluenesulfonamide (MYTsA, 0.24mmol), dichloromethane (DCM, 1mL) into a clean 4mL reaction flask, and stir at room temperature Followed by TLC; the reaction was completed in 2 hours. After the reaction, the solvent was concentrated and purified by column chromatography to obtain the target product 1a, a white solid, with a yield of 99%.
99% In dichloromethane at 20℃;
  • 53
  • [ 1005500-75-3 ]
  • [ 70396-20-2 ]
  • C24H37N3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In dichloromethane at 20℃; for 7h; 4 Synthesis of compound 4a Add Boc-Ala-Leu-OH (0.2mmol), N-ethynyl-N-methylp-toluenesulfonamide (MYTsA, 0.24mmol), dichloromethane (DCM, 1mL) into a clean 4mL reaction flask, at room temperature Under stirring, followed by TLC monitoring; the reaction was completed in 7 hours, after the reaction, the solvent was concentrated and separated and purified by column chromatography to obtain the target product, a white solid 4a, with a yield of 84%.
84% In dichloromethane at 20℃;
  • 54
  • [ 1005500-75-3 ]
  • [ 99-94-5 ]
  • C18H19NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% In dichloromethane at 20℃; for 24h; 5 Synthesis of compound 5a Add p-toluic acid (0.2mmol), N-ethynyl-N-methylp-toluenesulfonamide (MYTsA, 0.24mmol), dichloromethane (DCM, 1mL) into a clean 4mL reaction flask, stir at room temperature and use TLC follow-up monitoring; the reaction was completed within 24 hours, and after the reaction, the solvent was concentrated and purified by column chromatography to obtain the target product 5a, a white solid, with a yield of 97%.
With C35H50Br2N4O4; bis(trifluoromethane)sulfonimide lithium; holmium(III) triflate In chloroform at 20℃; for 2h; Molecular sieve; Inert atmosphere;
  • 55
  • [ 1005500-75-3 ]
  • [ 57-10-3 ]
  • C26H43NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In dichloromethane at 20℃; for 24h; 6 Synthesis of compound 6a Add hexadecanoic acid (0.2mmol), N-ethynyl-N-methyl-p-toluenesulfonamide (MYTsA, 0.24mmol), dichloromethane (DCM, 1mL) into a clean 4mL reaction flask, stir at room temperature and use TLC tracking and monitoring; the reaction was completed within 24 hours, and after the reaction, the solvent was concentrated and purified by column chromatography to obtain the target product 6a, a white solid, with a yield of 96%.
96% In dichloromethane at 20℃;
  • 56
  • [ 1005500-75-3 ]
  • C13H10(2)HNO2 [ No CAS ]
  • C23H21(2)HN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 57
  • [ 1005500-75-3 ]
  • [ 6092-74-6 ]
  • benzyl (2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 58
  • [ 1005500-75-3 ]
  • [ 28091-62-5 ]
  • methyl (2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 59
  • [ 1005500-75-3 ]
  • [ 58377-40-5 ]
  • tert-butyl (2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 60
  • [ 1005500-75-3 ]
  • [ 1503-92-0 ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)-4-methylphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 61
  • [ 1005500-75-3 ]
  • C20H27NO3Si [ No CAS ]
  • N-(4-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 62
  • [ 1005500-75-3 ]
  • [ 68221-23-8 ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)-4-methoxyphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 63
  • [ 1005500-75-3 ]
  • C18H20N2O4 [ No CAS ]
  • tert-butyl (4-benzamido-3-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 64
  • [ 1005500-75-3 ]
  • [ 67467-52-1 ]
  • methyl 4-benzamido-3-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 65
  • [ 1005500-75-3 ]
  • [ 34749-69-4 ]
  • N-(4-acetyl-2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 66
  • [ 1005500-75-3 ]
  • C13H10FNO2 [ No CAS ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)-4-fluorophenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 67
  • [ 1005500-75-3 ]
  • [ 1528-82-1 ]
  • N-(4-chloro-2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 68
  • [ 1005500-75-3 ]
  • [ 35021-82-0 ]
  • N-(4-bromo-2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 69
  • [ 1005500-75-3 ]
  • N-hydroxy-N-(4-(trifluoromethyl)phenyl)benzamide [ No CAS ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)-4-(trifluoromethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 70
  • [ 1005500-75-3 ]
  • C17H13NO3 [ No CAS ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)-4-(furan-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 71
  • [ 1005500-75-3 ]
  • C17H13NO2S [ No CAS ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)-4-(thiophen-3-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 72
  • [ 1005500-75-3 ]
  • [ 1143-74-4 ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)-6-methylphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 73
  • [ 1005500-75-3 ]
  • [ 90493-81-5 ]
  • N-(2-bromo-6-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 74
  • [ 1005500-75-3 ]
  • [ 29556-18-1 ]
  • N-(2-(2-((N,4-dimethylphenyl)sulfonamido)-2-oxoethyl)naphthalen-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 45℃; for 2h; Molecular sieve; Schlenk technique; Inert atmosphere; 2. Typical Procedure for the Synthesis of 3 and 4 General procedure: An oven-dried 25 mL Schlenk tube was charged with N-aryl hydroxamic acid 2 (1.5 eq., 0.3 mmol), Cu(OTf)2 (20 mol %, 0.04 mmol) and 4Å MS (50 mg), and the tube was evacuated and purged with argon for three times. Anhydrous DCE (1 mL) was added, and then a DCE solution (1 mL) of ynamide 1 (1.0 eq., 0.2 mmol) was added dropwise via syringe over 30 min. After stirring at 45 °C for 2 h, the reaction mixture was filtered through a short Celite pad. The filtrate was concentrated and purified by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:4 to 1:2) as eluent to afford the desired products 3 or 4.
  • 75
  • [ 1005500-75-3 ]
  • [ 3130-75-4 ]
  • 4-(1,3-dioxoisoindolin-2-yl)-N-methyl-N-(2-tosylacetyl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With Ir(dF(CF3)ppy)2(bpy)PF6 In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation;
  • 76
  • [ 1005500-75-3 ]
  • [ 5123-55-7 ]
  • (S)-2-(1,3-dioxoisoindolin-2-yl)-N-methyl-3-phenyl-N-(2-tosylacetyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With Ir(dF(CF3)ppy)2(bpy)PF6 In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation;
  • 77
  • [ 6964-21-2 ]
  • [ 1005500-75-3 ]
  • N-methyl-2-(thiophen-3-yl)-N-(2-tosylacetyl)acetamide [ No CAS ]
  • 78
  • [ 1005500-75-3 ]
  • C67H71IO12Si [ No CAS ]
  • C77H81NO14SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: C67H71IO12Si With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at -78℃; Inert atmosphere; Stage #2: N-ethynyl-N,4-dimethylbenzenesulfonamide In N,N-dimethyl-formamide at 67℃; Inert atmosphere; To a solution of the dimethylsilane-tethered disaccharide (100mg,0.082mmol) in a mixed solvent of DMF (1.0 mL) and Et3N (2.0mL)were added Pd(PPh3)2Cl2 (11mg, 0.016mmol), PPh3 (8 mg, 0.030mmol),and CuI (3 mg, 0.016mmol) successively. After being chilled to 78 C,the flask containing the reaction mixture was evacuated under reducedpressure and was then refilled with N2. After this process was repeatedfor 3 times, the reaction mixture was heated to 67 C by an oil bathe,to which a solution of methyltosylynamide (68mg, 0.325mmol) in dryDMF (1.0mL) was added dropwise at the same temperature under N2atmosphere. The stirring was continued overnight at the same temperaturebefore NH4Cl was added to quench the reaction. After being cooledto room temperature, the reaction mixture was extracted with ethyl acetatefor 3 times. The combined organic layer was washed with water andbrine, and was then dried over anhydrous Na2SO4. Filtration and concentrationin vacuo gave a residue, which was further purified by silicagel column chromatography (petroleum ether/ethyl acetate 8: 1) toafford pure 24 as a light yellow foam in 77% yield (82mg): [a]D25 8.6 (c 1.0, CHCl3); 1H NMR (400MHz, CDCl3) d 4.97 (dd, J2.0,6.8Hz, 2H), 7.66 (dd, J1.2, 8.4Hz, 1H), 7.54 (dd, J1.2, 7.2Hz,1H), 7.45 (d, J8.4Hz, 1H), 7.37 (dd, J1.6, 8.0Hz, 2H), 7.33-7.23(m, 23H), 7.18-7.13 (m, 7H), 7.10-7.06 (m, 3H), 5.23 (d, J7.6Hz,1H), 5.00 (d, J7.2Hz, 1H), 4.91 (t, J11.6Hz, 2 H), 4.78-4.53 (m,6H), 4.49 (d, J3.6Hz, 1H), 4.39 (d, J10.8 Hz, 1H), 4.29 (s, 2H),4.13-4.09 (m, 1 H), 3.88 (dd, J8.4, 9.6Hz, 1H), 3.73-3.64 (m, 4 H),3.62-3.58 (m, 2 H), 3.48-3.45 (m, 1 H), 3.38-3.30 (m, 3H), 3.19 (s, 3H),3.13 (s, 3 H), 2.35 (s, 3H), 0.12 (s, 3 H), 0.04 (s, 3H); 13C NMR(100MHz, CDCl3) d 154.1, 144.5, 139.0, 138.8, 138.7, 138.4, 138.2, 135.5(2C), 132.6, 129.8, 128.5 (3 C), 128.4, 128.3, 128.2, 128.1 (2C), 128.0,127.9 (2C), 127.7 (2C), 127.6 (3 C), 126.3, 125.6, 125.4, 123.3, 118.3(2C), 102.6, 97.9, 88.1, 85.8, 82.1, 80.1, 77.6 (2C), 75.9, 75.8, 75.5, 75.4,75.1, 74.8, 73.3, 71.7, 71.1, 68.6, 61.6, 55.0, 39.3, 21.7, 1.8, 2.4;HRMS (ESI) m/z calcd for C77H81O14NNaSSi [MNa]: 1326.5039;found: 1326.5027.
  • 79
  • [ 1005500-75-3 ]
  • [ 5783-59-5 ]
  • 8-methyltosylaminoethynyl-1-naphthyl methyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 1-iodo-8-methoxynaphthalene With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at -78℃; Inert atmosphere; Stage #2: N-ethynyl-N,4-dimethylbenzenesulfonamide In N,N-dimethyl-formamide at 67℃; Inert atmosphere; General procedure: To a solution of the dimethylsilane-tethered disaccharide (100mg,0.082mmol) in a mixed solvent of DMF (1.0 mL) and Et3N (2.0mL)were added Pd(PPh3)2Cl2 (11mg, 0.016mmol), PPh3 (8 mg, 0.030mmol),and CuI (3 mg, 0.016mmol) successively. After being chilled to 78 C,the flask containing the reaction mixture was evacuated under reducedpressure and was then refilled with N2. After this process was repeatedfor 3 times, the reaction mixture was heated to 67 C by an oil bathe,to which a solution of methyltosylynamide (68mg, 0.325mmol) in dryDMF (1.0mL) was added dropwise at the same temperature under N2atmosphere. The stirring was continued overnight at the same temperaturebefore NH4Cl was added to quench the reaction. After being cooledto room temperature, the reaction mixture was extracted with ethyl acetatefor 3 times. The combined organic layer was washed with water andbrine, and was then dried over anhydrous Na2SO4. Filtration and concentrationin vacuo gave a residue, which was further purified by silicagel column chromatography (petroleum ether/ethyl acetate 8: 1) toafford pure 24 as a light yellow foam in 77% yield (82mg): [a]D25 8.6 (c 1.0, CHCl3); 1H NMR (400MHz, CDCl3) d 4.97 (dd, J2.0,6.8Hz, 2H), 7.66 (dd, J1.2, 8.4Hz, 1H), 7.54 (dd, J1.2, 7.2Hz,1H), 7.45 (d, J8.4Hz, 1H), 7.37 (dd, J1.6, 8.0Hz, 2H), 7.33-7.23(m, 23H), 7.18-7.13 (m, 7H), 7.10-7.06 (m, 3H), 5.23 (d, J7.6Hz,1H), 5.00 (d, J7.2Hz, 1H), 4.91 (t, J11.6Hz, 2 H), 4.78-4.53 (m,6H), 4.49 (d, J3.6Hz, 1H), 4.39 (d, J10.8 Hz, 1H), 4.29 (s, 2H),4.13-4.09 (m, 1 H), 3.88 (dd, J8.4, 9.6Hz, 1H), 3.73-3.64 (m, 4 H),3.62-3.58 (m, 2 H), 3.48-3.45 (m, 1 H), 3.38-3.30 (m, 3H), 3.19 (s, 3H),3.13 (s, 3 H), 2.35 (s, 3H), 0.12 (s, 3 H), 0.04 (s, 3H); 13C NMR(100MHz, CDCl3) d 154.1, 144.5, 139.0, 138.8, 138.7, 138.4, 138.2, 135.5(2C), 132.6, 129.8, 128.5 (3 C), 128.4, 128.3, 128.2, 128.1 (2C), 128.0,127.9 (2C), 127.7 (2C), 127.6 (3 C), 126.3, 125.6, 125.4, 123.3, 118.3(2C), 102.6, 97.9, 88.1, 85.8, 82.1, 80.1, 77.6 (2C), 75.9, 75.8, 75.5, 75.4,75.1, 74.8, 73.3, 71.7, 71.1, 68.6, 61.6, 55.0, 39.3, 21.7, 1.8, 2.4;HRMS (ESI) m/z calcd for C77H81O14NNaSSi [MNa]: 1326.5039;found: 1326.5027.
  • 80
  • [ 1005500-75-3 ]
  • 8-iodo-1-naphthyl 2-O-(dimethyladamantoxysilyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside [ No CAS ]
  • 8-methyltosylaminoethynyl-1-naphthyl 2-O-(dimethyladamantoxysilyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 8-iodo-1-naphthyl 2-O-(dimethyladamantoxysilyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at -78℃; Inert atmosphere; Stage #2: N-ethynyl-N,4-dimethylbenzenesulfonamide In N,N-dimethyl-formamide at 65℃; Inert atmosphere; General procedure: To a solution of the dimethylsilane-tethered disaccharide (100mg,0.082mmol) in a mixed solvent of DMF (1.0 mL) and Et3N (2.0mL)were added Pd(PPh3)2Cl2 (11mg, 0.016mmol), PPh3 (8 mg, 0.030mmol),and CuI (3 mg, 0.016mmol) successively. After being chilled to 78 C,the flask containing the reaction mixture was evacuated under reducedpressure and was then refilled with N2. After this process was repeatedfor 3 times, the reaction mixture was heated to 67 C by an oil bathe,to which a solution of methyltosylynamide (68mg, 0.325mmol) in dryDMF (1.0mL) was added dropwise at the same temperature under N2atmosphere. The stirring was continued overnight at the same temperaturebefore NH4Cl was added to quench the reaction. After being cooledto room temperature, the reaction mixture was extracted with ethyl acetatefor 3 times. The combined organic layer was washed with water andbrine, and was then dried over anhydrous Na2SO4. Filtration and concentrationin vacuo gave a residue, which was further purified by silicagel column chromatography (petroleum ether/ethyl acetate 8: 1) toafford pure 24 as a light yellow foam in 77% yield (82mg): [a]D25 8.6 (c 1.0, CHCl3); 1H NMR (400MHz, CDCl3) d 4.97 (dd, J2.0,6.8Hz, 2H), 7.66 (dd, J1.2, 8.4Hz, 1H), 7.54 (dd, J1.2, 7.2Hz,1H), 7.45 (d, J8.4Hz, 1H), 7.37 (dd, J1.6, 8.0Hz, 2H), 7.33-7.23(m, 23H), 7.18-7.13 (m, 7H), 7.10-7.06 (m, 3H), 5.23 (d, J7.6Hz,1H), 5.00 (d, J7.2Hz, 1H), 4.91 (t, J11.6Hz, 2 H), 4.78-4.53 (m,6H), 4.49 (d, J3.6Hz, 1H), 4.39 (d, J10.8 Hz, 1H), 4.29 (s, 2H),4.13-4.09 (m, 1 H), 3.88 (dd, J8.4, 9.6Hz, 1H), 3.73-3.64 (m, 4 H),3.62-3.58 (m, 2 H), 3.48-3.45 (m, 1 H), 3.38-3.30 (m, 3H), 3.19 (s, 3H),3.13 (s, 3 H), 2.35 (s, 3H), 0.12 (s, 3 H), 0.04 (s, 3H); 13C NMR(100MHz, CDCl3) d 154.1, 144.5, 139.0, 138.8, 138.7, 138.4, 138.2, 135.5(2C), 132.6, 129.8, 128.5 (3 C), 128.4, 128.3, 128.2, 128.1 (2C), 128.0,127.9 (2C), 127.7 (2C), 127.6 (3 C), 126.3, 125.6, 125.4, 123.3, 118.3(2C), 102.6, 97.9, 88.1, 85.8, 82.1, 80.1, 77.6 (2C), 75.9, 75.8, 75.5, 75.4,75.1, 74.8, 73.3, 71.7, 71.1, 68.6, 61.6, 55.0, 39.3, 21.7, 1.8, 2.4;HRMS (ESI) m/z calcd for C77H81O14NNaSSi [MNa]: 1326.5039;found: 1326.5027.
Same Skeleton Products
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