(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

Base Information

• Chemical Name: (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
• CAS No.: 774598-87-7
• Molecular Formula: C₃₇H₄₀N₂O₁₀
• Molecular Weight: 672.732
• Mol file: 774598-87-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 90.0%

(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 (774598-86-6) + acetic anhydride (108-24-7) → (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 (774598-87-7)

Guidance literature:

With pyridine; at 20 ℃; for 26h;

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) → (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 (774598-87-7)

Guidance literature:

Multi-step reaction with 8 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

5: 66 percent / aq. KOH / dioxane / 45 h / Heating

6: 90 percent / pyridine / 19 h / 20 °C

7: 74 percent / HCOONH₄ / Pd/C / methanol / 6 h / Heating

8: 90 percent / pyridine / 26 h / 20 °C

With pyridine; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; N,O-bistrimethyl acetamide; ammonium formate; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; 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 → (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 (774598-87-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.05 g / pyridine / 20 h / 20 °C

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

3: 66 percent / aq. KOH / dioxane / 45 h / Heating

4: 90 percent / pyridine / 19 h / 20 °C

5: 74 percent / HCOONH₄ / Pd/C / methanol / 6 h / Heating

6: 90 percent / pyridine / 26 h / 20 °C

With pyridine; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; N,O-bistrimethyl acetamide; ammonium formate; palladium on activated charcoal; In 1,4-dioxane; methanol; acetonitrile;

DOI:10.1021/jo049159a

upstream raw materials:

(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

acetic anhydride

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

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