1-(2,3-DIDEOXY-BETA-D-GLYCEROPENT-2-ENOFURANOSYL)URACIL

Base Information

• Chemical Name: 1-(2,3-DIDEOXY-BETA-D-GLYCEROPENT-2-ENOFURANOSYL)URACIL
• CAS No.: 5974-93-6
• Molecular Formula: C9H10 N2 O4
• Molecular Weight: 210.189
• Mol file: 5974-93-6.mol

Synonyms:Uracil,1-(2,3-dideoxy-b-D-glycero-pent-2-enofuranosyl)-(7CI,8CI); 2',3'-Didehydro-2',3'-dideoxyuridine; 2',3'-Dideoxy-2',3'-didehydrouridine;2',3'-Dideoxyuridin-2'-ene; d4U

Chemical Property of 1-(2,3-DIDEOXY-BETA-D-GLYCEROPENT-2-ENOFURANOSYL)URACIL

Chemical Property:

• Vapor Pressure: 1.01E-09mmHg at 25°C
• Boiling Point: 443.4°C at 760 mmHg
• Flash Point: 221.9°C
• PSA: 84.32000
• Density: 1.448g/cm³
• LogP: -1.01750
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

2’,3’-Didehydro-2’,3’-dideoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2’,3’-Didehydro-2’,3’-dideoxyuridine, an nucleoside analog, is an anti-HIV drug.

Technology Process of 1-(2,3-DIDEOXY-BETA-D-GLYCEROPENT-2-ENOFURANOSYL)URACIL

There total 3 articles about 1-(2,3-DIDEOXY-BETA-D-GLYCEROPENT-2-ENOFURANOSYL)URACIL 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: 43.0%

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-uracil (42867-74-3) → uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 2',3'-dideoxy-2',3'-didehydrouridine (5974-93-6)

Guidance literature:

With ammonium hydroxide; In methanol; for 12h; Ambient temperature;

DOI:10.1021/jo00256a056

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 2',3'-dideoxy-2',3'-didehydrouridine (5974-93-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min

3: tetrahydrofuran / -78 °C

4: DIBAL-H / toluene / 2 h / -78 °C

5: 96 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 2 h, 2) 1,2-dichlorethane, a) 5 deg C, 10 min, b) room temperature, 10 min

7: 71 percent / 30percent aq. H₂O₂, pyridine / CH₂Cl₂ / Ambient temperature

8: 90 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00040a031

Reference yield:

→ 2,4-dihydroxypyrimidine (66-22-8,51953-14-1) + 2',3'-dideoxy-2',3'-didehydrouridine (5974-93-6)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00281a017

upstream raw materials:

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-uracil

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl)uracil

1-((2R,5S)-5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-3-(4-methoxy-benzyl)-1H-pyrimidine-2,4-dione

{(2S,5R)-5-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,5-dihydro-furan-2-ylmethoxymethyl}-phosphonic acid

{(2S,5R)-5-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,5-dihydro-furan-2-ylmethoxymethyl}-phosphonic acid diethyl ester