(E)-5-(2-Carboxyvinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil

Base Information

Chemical Name:(E)-5-(2-Carboxyvinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil
CAS No.:130351-62-1
Molecular Formula:C₁₃H₁₆N₂O₈
Molecular Weight:328.279
Hs Code.:

Synonyms:3'-OHCH2-Ara-5-Carboxyvinyl-U;130351-62-1;(E)-5-(2-Carboxyvinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil;2-Propenoic acid, 3-(1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl)-, (E)-;(E)-3-[1-[(2R,3S,4S,5S)-3-hydroxy-4,5-bis(hydroxymethyl)tetrahydrofuran-2-yl]-2,4-dioxo-pyrimidin-5-yl]prop-2-enoic acid;(E)-5-(2-Carboxyvinyl)-1-[3-deoxy-3-C-(hydroxymethyl)-.beta.-D-arabino-pentofuranosyl]uracil;2-Propenoic acid, 3-[1-[3-deoxy-3-(hydroxymethyl)-.beta.-D-arabinofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl]-, (E)-

Suppliers and Price of (E)-5-(2-Carboxyvinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil

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
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price

Total 1 raw suppliers

Chemical Property of (E)-5-(2-Carboxyvinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil

Chemical Property:

Density:1.675g/cm³
XLogP3:-2.2
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:328.09066547
Heavy Atom Count:23
Complexity:572

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=CC(=O)O
Isomeric SMILES:C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)CO)O)/C=C/C(=O)O

Technology Process of (E)-5-(2-Carboxyvinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil

There total 9 articles about (E)-5-(2-Carboxyvinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil 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: 55.0%

: 130351-61-0
(E)-5-<2-(carbomethoxy)vinyl>-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil

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

Guidance literature:: With sodium hydroxide; 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

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

Guidance literature:: Multi-step reaction with 7 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

With dmap; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; iodine; nitric acid; palladium diacetate; 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

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

Guidance literature:: Multi-step reaction with 9 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; iodine; nitric acid; palladium diacetate; 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