(1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:293751-12-9
Molecular Formula:C₁₉H₂₁N₅O₆S
Molecular Weight:447.472
Hs Code.:

Synonyms:(1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane

There total 12 articles about (1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-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: 95.0%

: C₂₂H₂₇N₅O₁₀S₂

: 293751-12-9
(1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;

Reference yield: 78.0%

: 293751-18-5
1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-6-N-benzoyladenine

: 293751-12-9
(1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With ammonium hydroxide; In 1,4-dioxane; at 20 ℃;
DOI:10.1021/jo010732p

Reference yield:

: 63593-03-3
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

: 293751-12-9
(1R,3R,4R,7S)-3-(adenine-9-yl)-7-benzyloxy-1-methanesulfonoxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / pyridine / 1 h / 20 °C

2.1: 97 percent / conc. H₂SO₄ / acetic acid / 24 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 1 h / Heating

3.2: 68 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 29 h / Heating

4.1: 78 percent / conc. NH₄OH / dioxane / 20 °C

With pyridine; ammonium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; In 1,4-dioxane; acetic acid; 1,2-dichloro-ethane;
DOI:10.1021/jo010732p