1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione
• CAS No.: 159626-11-6
• Molecular Formula: C₃₉H₃₉N₃O₁₁
• Molecular Weight: 725.752
• Mol file: 159626-11-6.mol

Synonyms:1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione

Chemical Property of 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione

There total 3 articles about 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>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: 83.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-3-(methoxymethyl)-5-(trifluoromethanesulfonyl)pyrrolo<2,3-d>pyrimidine-2,4-dione (159626-10-5) → 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione (159626-11-6)

Guidance literature:

With triethylamine; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide; at 68 ℃; for 2h;

DOI:10.1021/jo00102a011

Reference yield:

1-(Benzyloxy)methyl-5-(methoxycarbonyl)-3-(methoxymethyl)-7-(p-nitrophenethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione (165260-39-9) → 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione (159626-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80.5 percent / DBU / acetonitrile / Ambient temperature

2: NaH / acetonitrile / 1.) 45 deg C, 30 min, 2.) 1.5 h

With sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;

DOI:10.1021/jo00121a027

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 1-(Benzyloxy)methyl-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione (165260-40-2) → 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione (159626-11-6) + 1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione

Guidance literature:

With sodium hydride; In acetonitrile; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 1.) 45 deg C, 30 min, 2.) 1.5 h;

DOI:10.1021/jo00121a027

upstream raw materials:

methanol

carbon monoxide

1-<(Benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-3-(methoxymethyl)-5-(trifluoromethanesulfonyl)pyrrolo<2,3-d>pyrimidine-2,4-dione

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Downstream raw materials:

2-(Benzoylamino)-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidin-4-one

7-<2'-Deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)-3-(methoxymethyl)-2-(2,4,6-triisopropylbenzenesulfonyl)pyrrolo<2,3-d>pyrimidin-4-one

2-(Benzoylamino)-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-5-(methoxycarbonyl)pyrrolo<2,3-d>pyrimidin-4(3H)-one

3-Methoxymethyl-7-[(2R,4S,5R)-4-(4-methyl-benzoyloxy)-5-(4-methyl-benzoyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid methyl ester