1-(3-deoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-(3-deoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 114672-74-1
• Molecular Formula: C10H14 N2 O5
• Molecular Weight: 242.2286
• Mol file: 114672-74-1.mol

Synonyms:1-(b-D-3'-Deoxy-threo-pentofuranosyl)uracil;dAT

Chemical Property of 1-(3-deoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.452g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(3-deoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

There total 14 articles about 1-(3-deoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-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: 78.0%

(2S,3aS,9aR)-2-Hydroxymethyl-7-methyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one (134660-15-4) → 1-(3-deoxy-β-D-threo-pentofuranosyl)thymine (114672-74-1)

Guidance literature:

With methanol; sodium methylate; for 48h; Heating;

DOI:10.1055/s-1991-26454

Reference yield: 74.0%

5'-O-(4,4'-dimethoxytrityl)-1-(3-deoxy-β-D-arabinofuranosyl)thymine (114551-15-4) → 1-(3-deoxy-β-D-threo-pentofuranosyl)thymine (114672-74-1)

Guidance literature:

With acetic acid; at 22 ℃; for 0.5h;

DOI:10.1021/jm00402a038

Reference yield:

1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (138239-62-0) → 1-(3-deoxy-β-D-threo-pentofuranosyl)thymine (114672-74-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 1) ice-bath, 15 min; 2) 20 deg C, 3 h

2: aq. NaOH / ethanol / 1 h / 60 °C

3: 75 percent / LiEt₃BH / tetrahydrofuran / 1) dry ice/acetone cooling, 1 h; 2) 20 deg C, 1 h

4: 74 percent / aq. AcOH / 0.5 h / 22 °C

With pyridine; sodium hydroxide; lithium triethylborohydride; acetic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm00402a038

upstream raw materials:

(2S,3aS,9aR)-2-Hydroxymethyl-7-methyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

5'-O-(4,4'-dimethoxytrityl)-1-(3-deoxy-β-D-arabinofuranosyl)thymine

1,2-di-O-acetyl-5-O-(methoxycarbonyl)-3-deoxy-D-erythro-pentofuranose

Carbonic acid (2S,4R,5R)-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester methyl ester

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-1-(3-deoxy-β-D-arabinofuranosyl)thymine

1-{(2R,3S,5S)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

[(2S,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethyl]-phosphonic acid monomethyl ester