(2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile

Base Information

• Chemical Name: (2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile
• CAS No.: 121336-20-7
• Molecular Formula: C₃₀H₂₅N₃O₄
• Molecular Weight: 491.546

Synonyms:(2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile

Chemical Property of (2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile

Chemical Property:

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Technology Process of (2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile

There total 2 articles about (2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile 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:

1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine (115941-56-5) → (2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile (121336-20-7)

Guidance literature:

With 1,1'-Thiocarbonyldiimidazole; In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.3987/COM-88-4708

Reference yield:

1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine (115913-84-3) → (2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile (121336-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / tetrahydrofuran / Heating

2: N,N-thiocarbonyldiimidazole / dimethylformamide / 48 h / Ambient temperature

With 1,1'-Thiocarbonyldiimidazole; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.3987/COM-88-4708

Reference yield: 99.0%

(2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile (121336-20-7) → 1-(2',3'-dideoxy-3'-C-cyano-β-D-glyceropento-2'-enofuranosyl)thymine (118222-08-5)

Guidance literature:

With formic acid;

DOI:10.3987/COM-88-4708

upstream raw materials:

1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine

1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine

Downstream raw materials:

1-(3'-cyano-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine

1-(3'-cyano-2',3'-dideoxy-5'-O-trityl-β-D-threo-pentofuranosyl)thymine

1-(2',3'-dideoxy-3'-C-cyano-β-D-glyceropento-2'-enofuranosyl)thymine

1-(3'-C-cyano-2',3'-dideoxy-β-D-erythro-pentofuranosyl)thymine

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