N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide

Base Information

Chemical Name:N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide
CAS No.:171762-82-6
Molecular Formula:C₂₃H₃₁N₅O₁₀
Molecular Weight:537.527
Hs Code.:

N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide

Synonyms:N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide

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Chemical Property of N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide

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Technology Process of N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide

There total 2 articles about N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide 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:

: 55486-09-4
2'-O-Methyl-5-methyluridine

: 171762-82-6
N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / I₂, PPh₃, pyridine / 5 h / Ambient temperature

2: 89 percent / NaN₃ / dimethylformamide / 24 h / 60 °C

3: 87 percent / DMAP, imidazole / dimethylformamide / 24 h / Ambient temperature

4: 72 percent / SnCl₂*2H₂O / methanol / 20 h / Ambient temperature

5: 1.) Et₃N, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, HOBT, 2.) Et₃N / 1.) MeCN, THF, r.t., 1 h, 2.) r.t., 12 h

6: 91 percent / TBAF / tetrahydrofuran / 9 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium azide; tetrabutyl ammonium fluoride; iodine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; triphenylphosphine; tin(ll) chloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

Reference yield:

: 22423-26-3
O-2,2'-cyclo-5-methyluridine

: 171762-82-6
N-[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2-[(2S,3R,4R,5R)-2-hydroxymethyl-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 14 steps

1: 72 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 82 percent / Et₃N, DMAP, pyridine / CH₂Cl₂ / 40 h / Ambient temperature

3: 79 percent / AIBN / benzene / 20 h / Heating

4: 90 percent / aq. NaOH / tetrahydrofuran / 5 h / Ambient temperature

5: 92 percent / DBU / acetonitrile / 18 h / Ambient temperature

6: 83 percent / PPh₃, diisopropylazodicarboxylate / toluene / 50 h / Ambient temperature

7: 92 percent / NaOMe / methanol / 1 h / Ambient temperature

8: 94 percent / NaH / tetrahydrofuran / 17 h / Ambient temperature

9: 61 percent / OsO₄, N-methylmorpholine-N-oxide, H₂O / acetone / 18 h / Ambient temperature

10: 83 percent / H₂ / 10percent Pd/C / methanol / 18 h / 760 Torr / Ambient temperature

11: 81 percent / aq. NaIO₄ / dioxane / 18 h / Ambient temperature

12: 92 percent / aq. NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol / 30 h / Ambient temperature

13: 1.) Et₃N, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, HOBT, 2.) Et₃N / 1.) MeCN, THF, r.t., 1 h, 2.) r.t., 12 h

14: 91 percent / TBAF / tetrahydrofuran / 9 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; sodium hydride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;