1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 583844-08-0
• Molecular Formula: C₂₇H₂₈N₂O₇
• Molecular Weight: 492.529
• Mol file: 583844-08-0.mol

Synonyms:1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

There total 22 articles about 1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-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: 97.0%

3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine (457068-09-6) → 1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (583844-08-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo051187l

Reference yield:

(3aR,5S,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (136152-95-9) → 1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (583844-08-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 2.9 g / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

2: 65 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

3: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

4: NaIO₄; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

5: 754 mg / sodium tetrahydroborate / tetrahydrofuran; H₂O / 1 h / 0 °C

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

7: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

8: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

9: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

10: 87 percent / NaOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 - 20 °C

11: 73 percent / sodium hexamethyldisilazide / tetrahydrofuran / 6 h / Heating

12: 85 percent / MeOH; p-TsOH*H₂O / tetrahydrofuran / 1 h / 0 °C

13: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With methanol; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; water; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; methylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1: aldol-Cannizzaro reaction;

DOI:10.1021/jo051187l

Reference yield:

(R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol (583843-85-0) → 1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (583844-08-0)

Guidance literature:

Multi-step reaction with 14 steps

1: sodium periodate / tetrahydrofuran; H₂O / 0.75 h / 0 °C

2: 2.9 g / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

3: 65 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

4: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

5: NaIO₄; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

6: 754 mg / sodium tetrahydroborate / tetrahydrofuran; H₂O / 1 h / 0 °C

7: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

8: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

9: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

10: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

11: 87 percent / NaOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 - 20 °C

12: 73 percent / sodium hexamethyldisilazide / tetrahydrofuran / 6 h / Heating

13: 85 percent / MeOH; p-TsOH*H₂O / tetrahydrofuran / 1 h / 0 °C

14: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With methanol; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; water; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; methylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2: aldol-Cannizzaro reaction;

DOI:10.1021/jo051187l

upstream raw materials:

3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

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

3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-3-C-vinyl-α-D-ribofuranose

Downstream raw materials:

1-((2R,3S,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-hydroxy-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

1-((2R,3S,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-hydroxy-hexahydro-furo[2,3-c]pyran-2-yl)-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione

1-((2R,3S,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl)-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione

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