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

Base Information

Chemical Name:(1R,3R,4R,7S)-3-(guanin-9-yl)-7-benzyloxy-1-benzoyloxymethyl-2,5-dioxabicyclo-[2.2.1]heptane
CAS No.:709641-77-0
Molecular Formula:C₂₅H₂₃N₅O₆
Molecular Weight:489.488
Hs Code.:

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

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

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

There total 10 articles about (1R,3R,4R,7S)-3-(guanin-9-yl)-7-benzyloxy-1-benzoyloxymethyl-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%

: 532-32-1
sodium benzoate

: 293751-15-2
(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

: 709641-77-0
(1R,3R,4R,7S)-3-(guanin-9-yl)-7-benzyloxy-1-benzoyloxymethyl-2,5-dioxabicyclo-[2.2.1]heptane

Guidance literature:: In dimethyl sulfoxide; at 100 ℃; for 3.5h;
DOI:10.1016/j.bmc.2004.02.008

Reference yield:

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

: 709641-77-0
(1R,3R,4R,7S)-3-(guanin-9-yl)-7-benzyloxy-1-benzoyloxymethyl-2,5-dioxabicyclo-[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 90 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 3 h / Heating

2.1: 86 percent / sodium hydride; 3-hydroxypropionitrile / tetrahydrofuran / 4 h / 0 - 20 °C

3.1: 95 percent / dimethylsulfoxide / 3.5 h / 100 °C

With N,O-bis-(trimethylsilyl)-acetamide; sodium hydride; 3-Hydroxypropionitrile; In tetrahydrofuran; dimethyl sulfoxide; 1,2-dichloro-ethane; 1.1: Vorbrueggen coupling;
DOI:10.1016/j.bmc.2004.02.008

Reference yield:

: 405290-35-9
9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

: 709641-77-0
(1R,3R,4R,7S)-3-(guanin-9-yl)-7-benzyloxy-1-benzoyloxymethyl-2,5-dioxabicyclo-[2.2.1]heptane

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / sodium hydride; 3-hydroxypropionitrile / tetrahydrofuran / 4 h / 0 - 20 °C

2: 95 percent / dimethylsulfoxide / 3.5 h / 100 °C

With sodium hydride; 3-Hydroxypropionitrile; In tetrahydrofuran; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2004.02.008