2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-

Base Information

Chemical Name:2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-
CAS No.:130351-63-2
Molecular Formula:C₁₂H₁₅BrN₂O₆
Molecular Weight:363.165
Hs Code.:
Nikkaji Number:J343.692F

Synonyms:3'-Hydroxymethyl Ara-5-Br-vinyl-U;130351-63-2;(E)-5-(2-Bromovinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl uracil;2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-;SCHEMBL4952193;1-(3-Deoxy-3-hydroxymethyl-beta-D-arabinofuranosyl)-5-[(E)-2-bromoethenyl]uracil;(E)-5-(2-Bromovinyl)-1-[3-deoxy-3-C-(hydroxymethyl)-.beta.-D-arabino-pentofuranosyl uracil;2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-[3-deoxy-3-(hydroxymethyl)-.beta.-D-arabinofuranosyl]-, (E)-;5-[(E)-2-bromovinyl]-1-[(2R,3S,4S,5S)-3-hydroxy-4,5-bis(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Suppliers and Price of 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 3 raw suppliers

Chemical Property of 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-

Chemical Property:

Density:1.834g/cm³
XLogP3:-1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:362.01135
Heavy Atom Count:21
Complexity:494

Purity/Quality:: 85.0-99.8% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)CO)O)C=CBr
Isomeric SMILES:C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)CO)O)/C=C/Br

Technology Process of 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-

There total 10 articles about 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)- 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: 51.0%

: 130351-62-1
(E)-5-(2-carboxyvinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil

: 130351-63-2
(E)-5-(2-bromovinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil

Guidance literature:: With N-Bromosuccinimide; potassium carbonate; In N,N-dimethyl-formamide; for 0.5h; Ambient temperature;
DOI:10.1021/jm00171a025

Reference yield:

: 130351-52-9
1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil

: 130351-63-2
(E)-5-(2-bromovinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil

Guidance literature:: Multi-step reaction with 8 steps

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

3: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature

4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h

5: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating

6: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating

7: 55 percent / aq. NaOH / Ambient temperature

8: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; tetrabutyl ammonium fluoride; iodine; nitric acid; palladium diacetate; potassium carbonate; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00171a025

Reference yield:

: 96253-10-0
1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione

: 130351-63-2
(E)-5-(2-bromovinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min

2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature

3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

5: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature

6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h

7: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating

8: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating

9: 55 percent / aq. NaOH / Ambient temperature

10: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; iodine; nitric acid; palladium diacetate; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1021/jm00171a025