1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine

Base Information

• Chemical Name: 1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine
• CAS No.: 774598-83-3
• Molecular Formula: C₃₂H₄₀N₂O₁₃S₂
• Molecular Weight: 724.807
• Mol file: 774598-83-3.mol

Synonyms:1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine

Chemical Property of 1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine

There total 4 articles about 1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine 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: 93.0%

1,2-di-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-D-erythro-pentofuranose (774598-82-2) + thymin (65-71-4,28806-14-6,691841-57-3) → 1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine (774598-83-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; N,O-bistrimethyl acetamide; In acetonitrile; Heating;

DOI:10.1021/jo049159a

Reference yield:

3-O-benzyl-3-C-(3-benzyloxy)propyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (774598-81-1) → 1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine (774598-83-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 1 h / 20 °C

2: aq. TFA / 3 h / 20 °C

3: 2.05 g / pyridine / 20 h / 20 °C

4: 93 percent / N,O-bistrimethyl acetamide; trimethylsilyl triflate / acetonitrile / Heating

With pyridine; trimethylsilyl trifluoromethanesulfonate; N,O-bistrimethyl acetamide; trifluoroacetic acid; In acetonitrile;

DOI:10.1021/jo049159a

Reference yield:

Methanesulfonic acid (3S,4R)-3-benzyloxy-3-(3-benzyloxy-propyl)-4,5-dihydroxy-2-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester → 1-(2-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine (774598-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.05 g / pyridine / 20 h / 20 °C

2: 93 percent / N,O-bistrimethyl acetamide; trimethylsilyl triflate / acetonitrile / Heating

With pyridine; trimethylsilyl trifluoromethanesulfonate; N,O-bistrimethyl acetamide; In acetonitrile;

DOI:10.1021/jo049159a

upstream raw materials:

1,2-di-O-acetyl-3-O-benzyl-3-C-(3-benzyloxy)propyl-5-O-mesyl-4-C-mesyloxymethyl-D-erythro-pentofuranose

thymin

3-O-benzyl-3-C-(3-benzyloxy)propyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Downstream raw materials:

(1S,3R,4R,7S)-7-benzyloxy-7-(3-benzyloxy)propyl-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-7-(3-hydroxy)propyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-(3-acetoxypropyl)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane