(+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione

Base Information

Chemical Name:(+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione
CAS No.:95344-18-6
Molecular Formula:C₁₄H₁₈N₂O₆
Molecular Weight:310.307
Hs Code.:

Synonyms:(+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione

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Chemical Property of (+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione

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Technology Process of (+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione

There total 2 articles about (+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione 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: 15.0%

: 83967-03-7
C-IDU

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 62102-28-7
(+/-)-1-<(1β,3α,4β)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-2,4(1H,3H)-pyrimidinedione

: 95344-18-6
(+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione

Guidance literature:: With palladium diacetate; triethylamine; triphenylphosphine; In 1,4-dioxane; at 85 ℃; for 3.25h;
DOI:10.1021/jm50001a003

Reference yield:

: 59967-83-8
(+/-)-1-<(1β,2α,3α,4β)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-2,4-(1H,3H)-pyrimidinedione

: 95344-18-6
(+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-carbomethoxyvinyl>-2,4(1H,3H)-pyrimidinedione

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / diphenyl carbonate, sodium bicarbonate / hexamethylphosphoric acid triamide / 0.5 h / 150 °C

2: dimethylformamide; ethyl acetate / 1 h / Heating

3: tributyltin hydride, azobis(isobutyronitrile) / tetrahydrofuran / 0.75 h / Heating

4: sodium methoxide / methanol / Ambient temperature

5: iodine, 0.75 N aq. nitric acid / dioxane / 1 h / 100 °C

6: 80 percent / palladium(II) acetate, triphenylphosphine, triethylamine / dioxane / 3.25 h / 85 °C

With bis(phenyl) carbonate; 2,2'-azobis(isobutyronitrile); iodine; nitric acid; tri-n-butyl-tin hydride; sodium methylate; palladium diacetate; sodium hydrogencarbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm50001a003

Reference yield:

: 95344-18-6,120963-46-4,120963-47-5
(E)-3-[1-((1S,3S,4S)-3-Hydroxy-4-hydroxymethyl-cyclopentyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid methyl ester

: 1-((1S,3R,4R)-3-Azido-4-trityloxymethyl-cyclopentyl)-5-((E)-2-bromo-vinyl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / 2 M aq. KOH / 1.) RT, 9 h, 2.) 4 deg C, 24 h

2: 62 percent / N-bromosuccinimide, KHCO₃ / dimethylformamide / 1.5 h / Ambient temperature

3: 1.) pyridine / 1.) 80 deg C, 2.5 h, 2.) RT, 29 h

4: 78 percent / NaN₃ / dimethylformamide / 2 h / 85 °C

With pyridine; potassium hydroxide; N-Bromosuccinimide; sodium azide; potassium hydrogencarbonate; In N,N-dimethyl-formamide;
DOI:10.1039/c39900001547