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

Base Information

• Chemical Name: (E)-5-(2-(Methoxycarbonyl)vinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl)uracil
• CAS No.: 130351-61-0
• Molecular Formula: C₁₄H₁₈N₂O₈
• Molecular Weight: 342.306
• Mol file: 130351-61-0.mol

Synonyms:(3'-OHCH2 Ara-5-CH=CHCOOMe)U;130351-61-0;(E)-5-(2-(Methoxycarbonyl)vinyl)-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)-, methyl ester, (E)-;(E)-5-[2-(Methoxycarbonyl)vinyl]-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]-, methyl ester, (E)-;methyl (E)-3-[1-[(2R,3S,4S,5S)-3-hydroxy-4,5-bis(hydroxymethyl)tetrahydrofuran-2-yl]-2,4-dioxo-pyrimidin-5-yl]prop-2-enoate

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

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.547g/cm³
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 342.10631554
• Heavy Atom Count: 24
• Complexity: 587

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: COC(=O)C=CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)CO)O
• Isomeric SMILES: COC(=O)/C=C/C1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)CO)CO)O

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

There total 8 articles about (E)-5-(2-(Methoxycarbonyl)vinyl)-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: 38.0%

1-<3-deoxy-3C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>-5-iodouracil (130351-59-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-5-<2-(carbomethoxy)vinyl>-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-61-0) + 1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-54-1)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In 1,4-dioxane; for 1h; Heating;

DOI:10.1021/jm00171a025

Reference yield:

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil (130351-52-9) → (E)-5-<2-(carbomethoxy)vinyl>-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-61-0)

Guidance literature:

Multi-step reaction with 6 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

With dmap; 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:

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione (96253-10-0) → (E)-5-<2-(carbomethoxy)vinyl>-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-61-0)

Guidance literature:

Multi-step reaction with 8 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 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

upstream raw materials:

1-<3-deoxy-3C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>-5-iodouracil

acrylic acid methyl ester

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

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

Downstream raw materials:

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

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