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

Base Information

Chemical Name:(1R,3R,4S,7R)-7-benzyloxy-3-(guanin-9-yl)-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:410077-01-9
Molecular Formula:C₁₈H₁₉N₅O₅
Molecular Weight:385.379
Hs Code.:

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

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

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

There total 11 articles about (1R,3R,4S,7R)-7-benzyloxy-3-(guanin-9-yl)-1-hydroxymethyl-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: 35.0%

: 410077-00-8
2-N-acetyl-9-(3-O-benzyl-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-α-L-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)guanine

: 410077-01-9
(1R,3R,4S,7R)-7-benzyloxy-3-(guanin-9-yl)-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: 2-N-acetyl-9-(3-O-benzyl-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-α-L-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)guanine; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

With 18-crown-6 ether; potassium acetate; In 1,4-dioxane; at 80 ℃; for 18h;

With ammonia; In methanol; at 20 ℃; for 24h; Further stages.;
DOI:10.1021/ja0168763

Reference yield:

: 410076-93-6
3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose

: 410077-01-9
(1R,3R,4S,7R)-7-benzyloxy-3-(guanin-9-yl)-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 59 percent / trimethylsilyl trifluoromethanesulfonate / toluene

2.1: 95 percent / NH₃ / methanol

3.1: trifluoromethanesulfonic anhydride; pyridine / CH₂Cl₂

3.2: 63 percent / 18-crown-6 / toluene

4.1: 96 percent / NH₃ / methanol

5.1: sodium hydride / tetrahydrofuran

5.2: 18-crown-6 / dioxane

6.1: NH₃ / methanol

With pyridine; trimethylsilyl trifluoromethanesulfonate; ammonia; sodium hydride; trifluoromethanesulfonic acid anhydride; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1081/NCN-120022824

Reference yield:

: 410076-99-2
9-(2-O-acetyl-3-O-benzyl-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-α-L-erythro-pentofuranosyl)-2-N-acetyl-6-O-(diphenylcarbamoyl)guanine

: 410077-01-9
(1R,3R,4S,7R)-7-benzyloxy-3-(guanin-9-yl)-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / NH₃ / methanol

2.1: sodium hydride / tetrahydrofuran

2.2: 18-crown-6 / dioxane

3.1: NH₃ / methanol

With ammonia; sodium hydride; In tetrahydrofuran; methanol;
DOI:10.1081/NCN-120022824