(-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine

Base Information

Chemical Name:(-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine
CAS No.:290822-97-8
Molecular Formula:C₁₈H₁₇ClN₄O₃
Molecular Weight:372.811
Hs Code.:

Synonyms:

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Chemical Property of (-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine

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Technology Process of (-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine

There total 11 articles about (-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine 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:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 290822-97-8
(-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

1.2: 78 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 92 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

3.1: 77 percent / potassium hydroxide / methanol / 20 h / 20 °C

4.1: 80 percent / pyridine; chromium trioxide / CH₂Cl₂ / 20 °C

5.1: potassium carbonate; 18-crown-6 ether / benzene / 0.67 h / 56 °C

6.1: cerium(III) chloride heptahydrate; sodium borohydride / methanol / 0.25 h

7.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C

8.1: acetic acid / 24 h / 50 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; sodium hydride; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Metallation / 1.2: Addition / 2.1: Etherification / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Cyclization / 6.1: Reduction / 7.1: Substitution / 8.1: Hydrolysis;
DOI:10.1016/S0040-4020(00)00379-3

Reference yield:

: 117251-95-3
Dimethyl (6-O-benzyl-1-deoxy-3,4-O-isopropylidene-β-D-ribo-hex-2-ulofuranosyl)phosphonate

: 290822-97-8
(-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / potassium hydroxide / methanol / 20 h / 20 °C

2: 80 percent / pyridine; chromium trioxide / CH₂Cl₂ / 20 °C

3: potassium carbonate; 18-crown-6 ether / benzene / 0.67 h / 56 °C

4: cerium(III) chloride heptahydrate; sodium borohydride / methanol / 0.25 h

5: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C

6: acetic acid / 24 h / 50 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; 18-crown-6 ether; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; benzene; 1: Hydrolysis / 2: Oxidation / 3: Cyclization / 4: Reduction / 5: Substitution / 6: Hydrolysis;
DOI:10.1016/S0040-4020(00)00379-3

Reference yield:

: 290822-88-7
(-)-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-ribo-hexofuranose

: 290822-97-8
(-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

2: 77 percent / potassium hydroxide / methanol / 20 h / 20 °C

3: 80 percent / pyridine; chromium trioxide / CH₂Cl₂ / 20 °C

4: potassium carbonate; 18-crown-6 ether / benzene / 0.67 h / 56 °C

5: cerium(III) chloride heptahydrate; sodium borohydride / methanol / 0.25 h

6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C

7: acetic acid / 24 h / 50 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; 18-crown-6 ether; sodium hydride; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Etherification / 2: Hydrolysis / 3: Oxidation / 4: Cyclization / 5: Reduction / 6: Substitution / 7: Hydrolysis;
DOI:10.1016/S0040-4020(00)00379-3