1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:583844-13-7
Molecular Formula:C₃₅H₃₈N₂O₉
Molecular Weight:630.695
Hs Code.:

1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Synonyms:1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

There total 29 articles about 1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 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: 100.0%

: 583844-12-6
1-((2R,3S,3aS,7aS)-3a-Hydroxy-7a-hydroxymethyl-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

: 239808-67-4
4,4’-dimethoxytrityl trifluoromethanesulfonate

: 583844-13-7
1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1021/jo051187l

Reference yield: 58.0%

: 583844-12-6
1-((2R,3S,3aS,7aS)-3a-Hydroxy-7a-hydroxymethyl-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 583844-13-7
1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With silver trifluoromethanesulfonate; In tetrahydrofuran; pyridine; dichloromethane; at 20 ℃; for 8h;

Reference yield:

: 879546-87-9
3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

: 583844-13-7
1-{(2R,3S,3aS,7aR)-7a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3a-hydroxy-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 16 steps

1: 54 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

2: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

3: 25 percent / borane-1,4-oxathiane / 0 °C

4: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

5: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

6: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

7: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

8: 87 percent / NaOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 - 20 °C

9: 73 percent / sodium hexamethyldisilazide / tetrahydrofuran / 6 h / Heating

10: 85 percent / MeOH; p-TsOH*H₂O / tetrahydrofuran / 1 h / 0 °C

11: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

12: 67 percent / diisobutylaluminum hydride / tetrahydrofuran / 5 h / -78 °C

13: 68 percent / DBU / dimethylformamide / 3 h / 0 °C

14: 93 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

15: 63 percent / ammonium formate / Pd(OH)2/C / methanol / 7.5 h / Heating

16: 100 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; methanol; dmap; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; borane-1,4-oxathiane; sulfuric acid; ammonium formate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; methylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jo051187l