(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

Base Information

• Chemical Name: (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate
• CAS No.: 233266-86-9
• Molecular Formula: C₃₃H₄₀N₂O₇Si
• Molecular Weight: 604.775
• Mol file: 233266-86-9.mol

Synonyms:(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

Chemical Property of (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

There total 8 articles about (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate 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: 76.1%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-D-ribo-pentofuranose (233266-82-5) → (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate (233266-86-9)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 13h; Heating;

DOI:10.1021/jm000209n

Reference yield: 76.0%

1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-D-ribo-pentofuranose (233266-82-5) → (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate (233266-86-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane;

DOI:10.1271/bbb.63.1146

Reference yield:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate (233266-86-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂

2: 82 percent / PPh₃ / CH₂Cl₂

3: 88 percent / n-BuLi / tetrahydrofuran

4: 98 percent / n-BuLi / tetrahydrofuran

5: AcOH / H₂O

6: 80 percent / pyridine

7: 76 percent / TMSOTf / 1,2-dichloro-ethane

With n-butyllithium; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane; water; 1,2-dichloro-ethane; 1: Oxidation / 2: Substitution / 3: Elimination / 4: Substitution / 5: Hydrolysis / 6: Acetoxylation / 7: Substitution;

DOI:10.1271/bbb.63.1146

upstream raw materials:

1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-D-ribo-pentofuranose

uracil

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Downstream raw materials:

1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione