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

Base Information

• Chemical Name: 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose
• CAS No.: 233266-81-4
• Molecular Formula: C₂₅H₂₆O₇
• Molecular Weight: 438.477
• Mol file: 233266-81-4.mol

Synonyms:4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose

Chemical Property of 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose

There total 7 articles about 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose 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: 88.0%

acetic anhydride (108-24-7) + (3R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-5-ethynyl-tetrahydro-furan-2,3-diol → 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose (233266-81-4)

Guidance literature:

In pyridine;

DOI:10.1271/bbb.63.1146

Reference yield:

acetic anhydride (108-24-7) + 3,5-di-O-benzyl-4-C-ethynyl-1,2-O-isopropylidene-D-ribo-pentofuranose (233266-78-9) → 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose (233266-81-4)

Guidance literature:

With sulfuric acid; In ethyl acetate; at 20 ℃; Cooling with ice;

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) → 4-C-ethynyl-3,5-di-O-benzyl-1,2-di-O-acetyl-D-ribo-pentofuranose (233266-81-4)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 82 percent / PPh₃ / CH₂Cl₂

3: 88 percent / n-BuLi / tetrahydrofuran

4: AcOH / H₂O

5: 88 percent / pyridine

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

DOI:10.1271/bbb.63.1146

upstream raw materials:

acetic anhydride

((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

3,5-di-O-benzyl-4-C-ethynyl-1,2-O-isopropylidene-D-ribo-pentofuranose

Downstream raw materials:

1-(2-O-acetyl-3,5-di-O-benzyl-4-C-ethynyl-β-D-ribo-pentofuranosyl)thymine

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

1-(3,5-di-O-benzyl-4-C-ethynyl-β-D-arabino-pentofuranosyl)uracil

1-(2-O-acetyl-3,5-di-O-benzyl-4-C-ethynyl-β-D-ribo-pentofuranosyl)uracil