(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-chloropurine

Base Information

Chemical Name:(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-chloropurine
CAS No.:459867-39-1
Molecular Formula:C₂₅H₂₃ClN₄O₃
Molecular Weight:462.936
Hs Code.:

Synonyms:(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-chloropurine

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

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

There total 6 articles about (+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-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: 76.0%

: 459867-38-0
(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-(methoxy)methoxy-cyclopent-3-en-1-yl]-6-chloropurine

: 459867-39-1
(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-chloropurine

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1016/S0040-4020(02)00287-9

Reference yield:

: 100-39-0
benzyl bromide

: 459867-39-1
(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-chloropurine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 63 percent / NaH / dimethylformamide / 0.67 h / 0 °C

2.1: 100 percent / 60 percent AcOH / 24 h / 50 °C

3.1: CAN / CH₂Cl₂ / 2 h / 20 °C

3.2: 66 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4.1: 57 percent / PPh₃; DEAD / tetrahydrofuran / 16 h / 20 °C

5.1: 76 percent / TFA / CH₂Cl₂ / 16 h / 20 °C

With ammonium cerium(IV) nitrate; sodium hydride; acetic acid; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00287-9

Reference yield:

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

: 459867-39-1
(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-chloropurine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 63 percent / NaH / dimethylformamide / 0.67 h / 0 °C

2.1: 100 percent / 60 percent AcOH / 24 h / 50 °C

3.1: CAN / CH₂Cl₂ / 2 h / 20 °C

3.2: 66 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4.1: 57 percent / PPh₃; DEAD / tetrahydrofuran / 16 h / 20 °C

5.1: 76 percent / TFA / CH₂Cl₂ / 16 h / 20 °C

With ammonium cerium(IV) nitrate; sodium hydride; acetic acid; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00287-9