benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate

Base Information

• Chemical Name: benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate
• CAS No.: 140664-97-7
• Molecular Formula: C₃₀H₃₃FN₂O₁₅
• Molecular Weight: 680.595
• Mol file: 140664-97-7.mol

Synonyms:

Chemical Property of benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate

There total 4 articles about benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate 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: 18.0%

benzyl 2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosonate (121409-12-9) + 5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine (17242-85-2) → benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-α-D-galacto-2-nonulopyranosonate (140664-97-7,140665-01-6) + benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate (140664-97-7,140665-01-6)

Guidance literature:

With tin(IV) chloride; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1248/cpb.39.3140

Reference yield: 18.0%

benzyl 2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosonate (121409-12-9) + 5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine (17242-85-2) → benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-α-D-galacto-2-nonulopyranosonate (140664-97-7,140665-01-6) + benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate (140664-97-7,140665-01-6)

Guidance literature:

With tin(IV) chloride; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1248/cpb.39.3140

Reference yield:

benzyl 2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosonate (121409-12-9) → benzyl 4,5,7,8,9-penta-O-acetyl-2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-α-D-galacto-2-nonulopyranosonate (140664-97-7,140665-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / HCl(g), CH₃COOH, acetyl chloride / 8 h / Ambient temperature

2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 5 h

With hydrogenchloride; sodium hydride; acetic acid; acetyl chloride;

DOI:10.1248/cpb.39.3140

upstream raw materials:

5-fluorouracil

benzyl 4,5,7,8,9-penta-O-acetyl-2-chloro-2,3-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate

benzyl 2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosonate

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

Downstream raw materials:

benzyl 2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-β-D-galacto-2-nonulopyranosonate

benzyl 2,3-dideoxy-2-(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)-D-glycero-α-D-galacto-2-nonulopyranosonate