(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane
• CAS No.: 1092803-48-9
• Molecular Formula: C₃₉H₄₆N₂O₇Si
• Molecular Weight: 682.889
• Mol file: 1092803-48-9.mol

Synonyms:(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

There total 2 articles about (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[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: 96.0%

triethylsilyl chloride (994-30-9) + (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methylene-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane (1092803-47-8) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane (1092803-48-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/ja105875e

Reference yield:

(1R,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-5-methylene-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane (1092803-46-7) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane (1092803-48-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 16 h / 20 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

With pyridine; 1H-imidazole; In N,N-dimethyl-formamide;

Reference yield:

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane (1092803-48-9) → C39H47N3O6Si (1092804-55-1)

Guidance literature:

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-7-(triethylsilyloxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane; With 1,2,4-Triazole; triethylamine; trichlorophosphate; In acetonitrile; at 20 ℃; for 5h;

With ammonia; In 1,4-dioxane; water; at 20 ℃; for 4h;

DOI:10.1021/ja105875e

upstream raw materials:

triethylsilyl chloride

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methylene-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-5-methylene-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Downstream raw materials:

C₃₉H₄₇N₃O₆Si

C₃₃H₃₃N₃O₆

(1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methylene-2-oxabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane