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

Base Information

• Chemical Name: 1-((4aR,5R,7R,7aS)-4a-Benzyloxy-5-benzyloxymethyl-7a-hydroxy-hexahydro-furo[3,4-b]pyran-7-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 207568-87-4
• Molecular Formula: C₂₇H₃₀N₂O₇
• Molecular Weight: 494.544
• Mol file: 207568-87-4.mol

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

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

There total 3 articles about 1-((4aR,5R,7R,7aS)-4a-Benzyloxy-5-benzyloxymethyl-7a-hydroxy-hexahydro-furo[3,4-b]pyran-7-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: 94.0%

1-{(2R,4R,5R)-4-Benzyloxy-5-benzyloxymethyl-4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-oxo-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (207568-81-8) → 1-((4aR,5R,7R,7aS)-4a-Benzyloxy-5-benzyloxymethyl-7a-hydroxy-hexahydro-furo[3,4-b]pyran-7-yl)-5-methyl-1H-pyrimidine-2,4-dione (207568-87-4)

Guidance literature:

With triethylamine trihydrofluoride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1021/jo972239c

Reference yield:

1-[3,5-Di-O-benzyl-3-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine (199931-19-6) → 1-((4aR,5R,7R,7aS)-4a-Benzyloxy-5-benzyloxymethyl-7a-hydroxy-hexahydro-furo[3,4-b]pyran-7-yl)-5-methyl-1H-pyrimidine-2,4-dione (207568-87-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / pyridine / 2 h / Ambient temperature

2: 91 percent / pyridinium dichromate, molecular sieves 3A, acetic anhydride / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 94 percent / triethylamine trihydrofluoride / tetrahydrofuran / 12 h / Ambient temperature

With pyridine; dipyridinium dichromate; 3 A molecular sieve; triethylamine trihydrofluoride; acetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo972239c

Reference yield:

1-{(2R,3R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (207568-78-3) → 1-((4aR,5R,7R,7aS)-4a-Benzyloxy-5-benzyloxymethyl-7a-hydroxy-hexahydro-furo[3,4-b]pyran-7-yl)-5-methyl-1H-pyrimidine-2,4-dione (207568-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / pyridinium dichromate, molecular sieves 3A, acetic anhydride / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 94 percent / triethylamine trihydrofluoride / tetrahydrofuran / 12 h / Ambient temperature

With dipyridinium dichromate; 3 A molecular sieve; triethylamine trihydrofluoride; acetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo972239c

upstream raw materials:

1-{(2R,4R,5R)-4-Benzyloxy-5-benzyloxymethyl-4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-oxo-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

1-[3,5-Di-O-benzyl-3-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine

1-{(2R,3R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione