(αS)-5-[(DiMethylaMino)sulfonyl]-α-[[(9H-fluoren-9-ylMethoxy)carbonyl]aMino]-8-hydroxy-2-quinolinepropanoic Acid

Base Information

• Chemical Name: (αS)-5-[(DiMethylaMino)sulfonyl]-α-[[(9H-fluoren-9-ylMethoxy)carbonyl]aMino]-8-hydroxy-2-quinolinepropanoic Acid
• CAS No.: 607708-62-3
• Molecular Formula: C₂₉H₂₇N₃O₇S
• Molecular Weight: 561.615
• Mol file: 607708-62-3.mol

Synonyms:

Chemical Property of (αS)-5-[(DiMethylaMino)sulfonyl]-α-[[(9H-fluoren-9-ylMethoxy)carbonyl]aMino]-8-hydroxy-2-quinolinepropanoic Acid

Chemical Property:

• PKA: 2.84±0.10(Predicted)
• Density: 1.422±0.06 g/cm3(Predicted)

Purity/Quality:

98.5% ^*data from raw suppliers

(αS)-5-[(Dimethylamino)sulfonyl]-α-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-8-hydroxy-2-quinolinepropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A modular and tunable chemosensor Scaffold for divalent zinc. Selective and tunable chemosensors for selected transition metal ions have the potential to afford qualitative and quantitative information about the presemce, distribution and concentration of these metal ions in cells or tissues. Sensing divalent zinc is particulary desirable because of its physiological importance.

Technology Process of (αS)-5-[(DiMethylaMino)sulfonyl]-α-[[(9H-fluoren-9-ylMethoxy)carbonyl]aMino]-8-hydroxy-2-quinolinepropanoic Acid

There total 8 articles about (αS)-5-[(DiMethylaMino)sulfonyl]-α-[[(9H-fluoren-9-ylMethoxy)carbonyl]aMino]-8-hydroxy-2-quinolinepropanoic Acid 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: 74.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-2-amino-3-(8-hydroxy-5-(N,N-dimethyl)sulfonamidoquinoline-2-yl)propionic acid hydrochloride → (S)-2-amino-Nα-(9-fluorenylmethyloxycarbonyl)-3-(8-hydroxy-5-(N,N-dimethyl)sylfonamidoquinoline-2-yl)propionic acid (607708-62-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; for 18h;

DOI:10.1021/ja0355980

Reference yield:

5-(N,N-dimethyl)sulfonamido-8-hydroxy-2-methylquinoline (349543-92-6) → (S)-2-amino-Nα-(9-fluorenylmethyloxycarbonyl)-3-(8-hydroxy-5-(N,N-dimethyl)sylfonamidoquinoline-2-yl)propionic acid (607708-62-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 57 percent / imidazole / dimethylformamide / 2 h

2: 4A moleculer sieves; selenium dioxide / dioxane / 17 h / 95 °C

3: sodium borohydride / ethanol; CH₂Cl₂ / 0.25 h

4: 538 mg / N-bromosuccinimide; triphenylphosphine / CH₂Cl₂ / 4 h / 0 °C

5: (8S,9R)-O-⁽⁹⁾-allyl-N-9-anthracenyl methylcinchonidium Br; cesium hydrochloride monohydrate / CH₂Cl₂ / 51 h / -78 - -55 °C

6: aq. HCl / 2 h / Heating

7: 74 percent / aq. sodium bicarbonate / dioxane / 18 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; selenium(IV) oxide; (1S,2S,4S,5R)-2-((R)-(allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide; 4 A molecular sieve; cesium hydrochloride monohydrate; sodium hydrogencarbonate; triphenylphosphine; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0355980

Reference yield:

8-hydroxy-2-methyl-quinoline-5-sulfonyl chloride (903877-94-1) → (S)-2-amino-Nα-(9-fluorenylmethyloxycarbonyl)-3-(8-hydroxy-5-(N,N-dimethyl)sylfonamidoquinoline-2-yl)propionic acid (607708-62-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / tetrahydrofuran / 3.17 h

2: 57 percent / imidazole / dimethylformamide / 2 h

3: 4A moleculer sieves; selenium dioxide / dioxane / 17 h / 95 °C

4: sodium borohydride / ethanol; CH₂Cl₂ / 0.25 h

5: 538 mg / N-bromosuccinimide; triphenylphosphine / CH₂Cl₂ / 4 h / 0 °C

6: (8S,9R)-O-⁽⁹⁾-allyl-N-9-anthracenyl methylcinchonidium Br; cesium hydrochloride monohydrate / CH₂Cl₂ / 51 h / -78 - -55 °C

7: aq. HCl / 2 h / Heating

8: 74 percent / aq. sodium bicarbonate / dioxane / 18 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; selenium(IV) oxide; (1S,2S,4S,5R)-2-((R)-(allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide; 4 A molecular sieve; cesium hydrochloride monohydrate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0355980

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

5-(N,N-dimethyl)sulfonamido-8-hydroxy-2-methylquinoline

8-hydroxy-2-methyl-quinoline-5-sulfonyl chloride

8-tert-butyldiphenylsilyloxy-5-(N,N-dimethyl)sulfonamido-2-methylquinoline