4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: 4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 133635-50-4
• Molecular Formula: C₁₈H₂₀N₂O₆
• Molecular Weight: 360.367
• Mol file: 133635-50-4.mol

Synonyms:

Chemical Property of 4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

There total 5 articles about 4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 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%

methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside (133635-44-6) + (2,4-Bis-trimethylsilanyloxy-pyrimidin-5-yl)-methanol (111878-20-7) → 4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (133635-50-4,133697-35-5) + 1-(2,3-dideoxy-5-O-(4-methylbenzoyl)-α-D-glycero-pentofuranosyl)-5-hydroxymethyluracil (133698-19-8) + 2',3'-dideoxy-5'-O-(4-methylbenzoyl)-5-hydroxymethyluridine (133635-55-9,133698-19-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Ambient temperature;

DOI:10.1007/BF00815166

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (133635-50-4,133697-35-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 42 percent / pyridine / a) r.t., 0.5h, b) 80 deg C, 3h

2: DIBAL / tetrahydrofuran; hexane / 0.5 h / -75 °C

3: 0.2 percent HCl / 0.25 h / Ambient temperature

4: trimethylsilyl triflate / CH₂Cl₂ / Ambient temperature

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1007/BF00815166

Reference yield:

((2S)-5-hydroxyoxolan-2-yl)methyl 4-methylbenzoate → 4-Methyl-benzoic acid (S)-5-(5-hydroxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (133635-50-4,133697-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.2 percent HCl / 0.25 h / Ambient temperature

2: trimethylsilyl triflate / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1007/BF00815166

upstream raw materials:

methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside

(2,4-Bis-trimethylsilanyloxy-pyrimidin-5-yl)-methanol

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

(S)-γ-(4-methylbenzoyloxymethyl)-γ-butyrolactone