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

Base Information

• Chemical Name: 1-{(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 485755-37-1
• Molecular Formula: C₄₂H₄₄N₂O₉
• Molecular Weight: 720.819
• Mol file: 485755-37-1.mol

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

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

There total 12 articles about 1-{(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-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: 89.0%

Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (485755-36-0) → 1-{(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (485755-37-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1039/b205031e

Reference yield:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (197702-06-0) → 1-{(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (485755-37-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₅IO₆ / ethyl acetate

1.2: aq. NaOH / tetrahydrofuran

1.3: 82 percent / NaBH₄

2.1: 85 percent / DMAP / pyridine

3.1: aq. AcOH / 90 °C

4.1: DMAP / pyridine

5.1: 67 percent / N,O-bis(trimethylsilyl)acetamide; TMS-triflate / acetonitrile / 60 °C

6.1: 81 percent / NaOMe / methanol

7.1: 70 percent / pyridine

8.1: pyridine

9.1: NaH / tetrahydrofuran

10.1: aq. OsO₄; NaIO₄ / dioxane

11.1: NaBH₄ / H₂O; dioxane

12.1: 89 percent / NaH / dimethylformamide

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; periodic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b205031e

Reference yield:

3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (457067-99-1) → 1-{(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (485755-37-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / DMAP / pyridine

2: aq. AcOH / 90 °C

3: DMAP / pyridine

4: 67 percent / N,O-bis(trimethylsilyl)acetamide; TMS-triflate / acetonitrile / 60 °C

5: 81 percent / NaOMe / methanol

6: 70 percent / pyridine

7: pyridine

8: NaH / tetrahydrofuran

9: aq. OsO₄; NaIO₄ / dioxane

10: NaBH₄ / H₂O; dioxane

11: 89 percent / NaH / dimethylformamide

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b205031e

upstream raw materials:

Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose