(3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate

Base Information

• Chemical Name: (3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate
• CAS No.: 80581-75-5
• Molecular Formula: C₁₉H₂₂O₉
• Molecular Weight: 394.378
• Mol file: 80581-75-5.mol

Synonyms:(3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate

Chemical Property of (3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate

There total 17 articles about (3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate 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: 63.5%

acetic anhydride (108-24-7) + 5-O-benzoyl-3-C-methyl-α,β-D-ribofuranose (89157-83-5,89157-84-6) → 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose (60374-77-8,80581-75-5,89195-77-7,115269-09-5,115269-10-8) + 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose (89195-77-7)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 72h;

DOI:10.1016/0008-6215(88)84024-2

Reference yield:

acetic anhydride (108-24-7) + ((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate (89157-83-5) → (3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate (80581-75-5)

Guidance literature:

With pyridine; dmap; at 20 ℃;

Reference yield:

acetic anhydride (108-24-7) + 3-O-acetyl-5-O-benzoyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose (80541-14-6) → 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose (60374-77-8,80581-75-5,89195-77-7,115269-09-5,115269-10-8) + 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose (89195-77-7)

Guidance literature:

With sulfuric acid; In acetic acid; at 20 ℃; for 96h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0008-6215(83)88357-8

upstream raw materials:

acetic anhydride

5-O-benzoyl-3-C-methyl-α,β-D-ribofuranose

3-O-acetyl-5-O-benzoyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose

((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Downstream raw materials:

4-chloro-5-cyano-7-(2',3'-di-O-acetyl-5'-O-benzoyl-3'-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose

6-chloro-9-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)-9H-purin-2-amine

1-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil