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

Base Information

Chemical Name:(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:293751-10-7
Molecular Formula:C₂₃H₂₇N₅O₈S
Molecular Weight:533.562
Hs Code.:

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

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

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

There total 8 articles about (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-9-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: 78.0%

: 293751-14-1
9-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-N-isobutyrylguanine

: 293751-10-7
(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With sodium hydroxide; water; In 1,4-dioxane; at 20 ℃; for 0.25h; Product distribution / selectivity;

Reference yield:

: 21047-89-2
2-N-isobutyrylguanine

: 293751-03-8
1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

: 293751-10-7
(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: 2-N-isobutyrylguanine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In 1,2-dichloro-ethane; for 1.5h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 2h; Heating;

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 1h; Further stages.;
DOI:10.1021/jo010732p

Reference yield:

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

: 293751-10-7
(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 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 / 1.5 h / Heating

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

3.3: 6.9 g / aq. NaOH / tetrahydrofuran / 1 h / 0 °C

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