(1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane

Base Information

Chemical Name:(1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane
CAS No.:175471-22-4
Molecular Formula:C₂₃H₂₉N₅O₂
Molecular Weight:407.516
Hs Code.:

Synonyms:(1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane

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Chemical Property of (1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane

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Technology Process of (1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane

There total 6 articles about (1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane 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: 76.0%

: 175471-21-3
(1S,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-chloro-9-purinyl)bicyclo<3.1.0>hexane

: 175471-22-4
(1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane

Guidance literature:: With ammonium hydroxide; In 1,4-dioxane; at 65 ℃; for 14h;
DOI:10.1080/07328319608002382

Reference yield:

: 89291-76-9
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

: 175471-22-4
(1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 8 steps

1: 54 percent / CH₂Cl₂; toluene / -78 deg C, rt, 18 h

2: 87.4 percent / imidazole / dimethylformamide / 0.67 h / Ambient temperature

3: 2.) NaH / 1.) THF, 0 deg C, 5 min, 2.) rt, 60 min

4: 77 percent / AIBN, n-Bu₃SnH / toluene / 1.5 h / Heating

5: 92 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature; overnight

6: 96 percent / Sm, HgCl₂ / CH₂Cl₂; tetrahydrofuran / -78 deg C to rt

7: 1.) Ph₃P, DEAD / 1.) THF, rt, 20 min, 2.) 72 h

8: 76 percent / conc. NH₄OH / dioxane / 14 h / 65 °C

With 1H-imidazole; ammonium hydroxide; samarium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; triphenylphosphine; mercury dichloride; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1080/07328319608002382

Reference yield:

: 169191-14-4
(1S,4R,5S)-3-<(benzyloxy)methyl>-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol

: 175471-22-4
(1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 7 steps

1: 87.4 percent / imidazole / dimethylformamide / 0.67 h / Ambient temperature

2: 2.) NaH / 1.) THF, 0 deg C, 5 min, 2.) rt, 60 min

3: 77 percent / AIBN, n-Bu₃SnH / toluene / 1.5 h / Heating

4: 92 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature; overnight

5: 96 percent / Sm, HgCl₂ / CH₂Cl₂; tetrahydrofuran / -78 deg C to rt

6: 1.) Ph₃P, DEAD / 1.) THF, rt, 20 min, 2.) 72 h

7: 76 percent / conc. NH₄OH / dioxane / 14 h / 65 °C

With 1H-imidazole; ammonium hydroxide; samarium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; triphenylphosphine; mercury dichloride; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1080/07328319608002382