Welcome to LookChem.com Sign In|Join Free

Cas Database

174455-55-1

174455-55-1

Identification

Synonyms:1-[5-(Acetyloxy)hexyl]-3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione;;

Post Buying Request Now

Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:5’-O-Acetyl(R)-Lisofylline
  • Packaging:10 mg
  • Price:$ 130
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:5’-O-Acetyl(R)-Lisofylline
  • Packaging:5mg
  • Price:$ 90
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:5’-O-Acetyl(R)-Lisofylline
  • Packaging:100 mg
  • Price:$ 990
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:5?-O-Acetyl(R)-Lisofylline
  • Packaging:10 mg
  • Price:$ 875
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:5'-O-Acetyl (R)-lisofylline
  • Packaging:100 mg
  • Price:$ 1365
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:5'-O-Acetyl (R)-lisofylline
  • Packaging:5 mg
  • Price:$ 124.9
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:5'-O-Acetyl (R)-lisofylline
  • Packaging:50 mg
  • Price:$ 751
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:5'-O-Acetyl (R)-lisofylline
  • Packaging:25 mg
  • Price:$ 413
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:5'-O-Acetyl (R)-lisofylline
  • Packaging:10 mg
  • Price:$ 227.2
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 2 Articles be found

Chemoenzymatic enantioselective and stereo-convergent syntheses of lisofylline enantiomers via lipase-catalyzed kinetic resolution and optical inversion approach

Borowiecki, Pawe?,Zdun, Beata,Dranka, Maciej

, (2021/02/27)

Highly enantioselective enzymatic kinetic resolution (EKR) of racemic lisofylline is presented for the first time. A comprehensive optimization of the key parameters of lipase-catalyzed transesterification of racemic lisofylline revealed that optimal biocatalytic system consisted of immobilized lipase type B from Candida antarctica (Chirazyme L-2, C-3) suspended in a mixture of 3 equiv of vinyl acetate as an acetyl donor and ethyl acetate as a solvent. Under optimal reaction conditions, the 1 g-scale (Chirazyme L-2, C-3)-catalyzed kinetic resolution of racemic lisofylline furnished both the EKR products in a homochiral form (>99 % ee) with the 50 % conv., and the highest possible enantioselectivity. The best results in terms of the reaction yields (47–50 %) and enantiomeric purity of the kinetically-resolved optically active products were achieved when the preparative-scale EKR was carried out for 2 h at 60 °C. In addition, stereoinversion of the less biologically-relevant (S)-lisofylline into its (R)-enantiomer was successfully achieved via acetolysis of the respective optically pure (S)-mesylate by using 2 equiv of ceasium acetate and catalytic amount of 18-Crown-6 in dry toluene, followed by K2CO3-mediated methanolysis of (R)-acetate. The elaborated EKR methodology together with enantioconvergent strategy provided a useful chemoenzymatic protocol for the synthesis of complementary enantiomers of titled API. Moreover, we report on the first single-crystal X-ray diffraction (XRD) analyses performed for the synthesized lisofylline enantiomers. Insight into the source of CAL-B stereoselectivity toward racemic lisofylline was gained by molecular docking experiments. In silico theoretical predictions matched very well with experimental results.

Process route upstream and downstream products

Process route

vinyl acetate
108-05-4,9003-20-7

vinyl acetate

1-(5-hydroxyhexyl)theobromine
6493-06-7,100324-80-9,100324-81-0

1-(5-hydroxyhexyl)theobromine

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

lisofylline
100324-81-0

lisofylline

(+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione
100324-80-9

(+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione

Conditions
Conditions Yield
With immobilized Candida antarctica type B lipase Chirazyme L-2, C-3; In chloroform; at 60 ℃; for 1h; enantioselective reaction; Sealed tube;
89 % ee
99 % ee
vinyl acetate
108-05-4,9003-20-7

vinyl acetate

1-(5-hydroxyhexyl)theobromine
6493-06-7,100324-80-9,100324-81-0

1-(5-hydroxyhexyl)theobromine

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

(+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione
100324-80-9

(+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione

Conditions
Conditions Yield
With immobilized Candida antarctica type B lipase Chirazyme L-2, C-3; In ethyl acetate; at 40 ℃; for 8h; Reagent/catalyst; Solvent; Temperature; enantioselective reaction; Sealed tube;
>99 % ee
99 % ee
acetyl chloride
75-36-5

acetyl chloride

1-(5-hydroxyhexyl)theobromine
6493-06-7,100324-80-9,100324-81-0

1-(5-hydroxyhexyl)theobromine

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 24h;
40%
lisofylline
301329-26-0

lisofylline

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
With 18-crown-6 ether; cesium acetate; In toluene; at 110 ℃; for 18h;
50%
theobromine /
83-67-0

theobromine /

C<sub>9</sub>H<sub>18</sub>O<sub>5</sub>S

C9H18O5S

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
With sodium hydride; In dimethyl sulfoxide; at 60 ℃; for 20h; Inert atmosphere;
6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
With Chiralpak AD-H; In hexane; isopropyl alcohol; at 25 ℃; Resolution of racemate;
6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
With Chiralpak AD-H; In hexane; isopropyl alcohol; at 25 ℃; Resolution of racemate;
pentoxyphylline
6493-05-6

pentoxyphylline

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; dichloromethane / 0.67 h / 0 - 5 °C
2: immobilized Candida antarctica type B lipase Chirazyme L-2, C-3 / ethyl acetate / 8 h / 40 °C / Sealed tube
With sodium tetrahydroborate; In methanol; dichloromethane; ethyl acetate;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; dichloromethane / 0.67 h / 0 - 5 °C
2: immobilized Candida antarctica type B lipase Chirazyme L-2, C-3 / chloroform / 1 h / 60 °C / Sealed tube
With sodium tetrahydroborate; In methanol; dichloromethane; chloroform;
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol; dichloromethane / 0.67 h / 0 - 5 °C
2: triethylamine; dmap / dichloromethane / 24 h / 0 - 20 °C
3: Chiralpak AD-H / hexane; isopropyl alcohol / 25 °C / Resolution of racemate
With dmap; sodium tetrahydroborate; triethylamine; In methanol; hexane; dichloromethane; isopropyl alcohol;
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol; dichloromethane / 0.67 h / 0 - 5 °C
2: triethylamine / dichloromethane / 1.17 h / 0 - 20 °C
3: cesium acetate; 18-crown-6 ether / toluene / 18 h / 110 °C
With sodium tetrahydroborate; 18-crown-6 ether; cesium acetate; triethylamine; In methanol; dichloromethane; toluene;
Ethyl 5-hydroxyhexanoate
20266-62-0

Ethyl 5-hydroxyhexanoate

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: C50H63ClIrN2P; potassium tert-butylate; hydrogen / ethanol / 0.25 h / 25 - 30 °C / 7600.51 Torr / Autoclave; Green chemistry
2: triethylamine / dichloromethane / 2 h / -20 °C / Inert atmosphere
3: triethylamine; dmap / tetrahydrofuran / 20 °C
4: sodium hydride / dimethyl sulfoxide / 20 h / 60 °C / Inert atmosphere
With dmap; C50H63ClIrN2P; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 4 steps
1: C50H63ClIrN2P; potassium tert-butylate; hydrogen / ethanol / 1 h / 25 - 30 °C / 7600.51 Torr / Autoclave; Green chemistry
2: triethylamine / dichloromethane / 2 h / -20 °C / Inert atmosphere
3: triethylamine; dmap / tetrahydrofuran / 20 °C
4: sodium hydride / dimethyl sulfoxide / 20 h / 60 °C / Inert atmosphere
With dmap; C50H63ClIrN2P; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 4 steps
1: C50H63ClIrN2P; potassium tert-butylate; hydrogen / ethanol / 2 h / 25 - 30 °C / 7600.51 Torr / Autoclave; Green chemistry
2: triethylamine / dichloromethane / 2 h / -20 °C / Inert atmosphere
3: triethylamine; dmap / tetrahydrofuran / 20 °C
4: sodium hydride / dimethyl sulfoxide / 20 h / 60 °C / Inert atmosphere
With dmap; C50H63ClIrN2P; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
ethyl 5-oxohexanoate
13984-57-1

ethyl 5-oxohexanoate

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate
174455-55-1

6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: sodium tetrahydroborate; ethanol / 0.12 h / 0 °C
2: C50H63ClIrN2P; potassium tert-butylate; hydrogen / ethanol / 0.25 h / 25 - 30 °C / 7600.51 Torr / Autoclave; Green chemistry
3: triethylamine / dichloromethane / 2 h / -20 °C / Inert atmosphere
4: triethylamine; dmap / tetrahydrofuran / 20 °C
5: sodium hydride / dimethyl sulfoxide / 20 h / 60 °C / Inert atmosphere
With dmap; sodium tetrahydroborate; ethanol; C50H63ClIrN2P; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 5 steps
1: sodium tetrahydroborate; ethanol / 0.12 h / 0 °C
2: C50H63ClIrN2P; potassium tert-butylate; hydrogen / ethanol / 1 h / 25 - 30 °C / 7600.51 Torr / Autoclave; Green chemistry
3: triethylamine / dichloromethane / 2 h / -20 °C / Inert atmosphere
4: triethylamine; dmap / tetrahydrofuran / 20 °C
5: sodium hydride / dimethyl sulfoxide / 20 h / 60 °C / Inert atmosphere
With dmap; sodium tetrahydroborate; ethanol; C50H63ClIrN2P; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 5 steps
1: sodium tetrahydroborate; ethanol / 0.12 h / 0 °C
2: C50H63ClIrN2P; potassium tert-butylate; hydrogen / ethanol / 2 h / 25 - 30 °C / 7600.51 Torr / Autoclave; Green chemistry
3: triethylamine / dichloromethane / 2 h / -20 °C / Inert atmosphere
4: triethylamine; dmap / tetrahydrofuran / 20 °C
5: sodium hydride / dimethyl sulfoxide / 20 h / 60 °C / Inert atmosphere
With dmap; sodium tetrahydroborate; ethanol; C50H63ClIrN2P; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;

Global suppliers and manufacturers

Global( 4) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Finetech Industry Limited
  • Business Type:Trading Company
  • Contact Tel:86-27-87465837
  • Emails:sales@finetechnology-ind.com
  • Main Products:29
  • Country:China (Mainland)
  • BOC Sciences
  • Business Type:Trading Company
  • Contact Tel:1-631-485-4226
  • Emails:sales@bocsci.com
  • Main Products:41
  • Country:United States
  • PRIME MOLECULAR CO.,LIMITED
  • Business Type:Trading Company
  • Contact Tel:0852-0755-61104662
  • Emails:sales@prime-molecular.com
  • Main Products:1
  • Country:China (Mainland)
  • Toronto Research Chemicals
  • Business Type:Trading Company
  • Contact Tel:(416) 665-9696, 800-727-9240
  • Emails:torresch@interlog.com
  • Main Products:1
  • Country:Canada
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 174455-55-1
Post Buying Request Now
close
Remarks: The blank with*must be completed