(1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

Base Information

Chemical Name:(1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine
CAS No.:288103-13-9
Molecular Formula:C₂₄H₂₇N₅O₃
Molecular Weight:433.51
Hs Code.:

Synonyms:(1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

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Chemical Property of (1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

Chemical Property:

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Technology Process of (1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

There total 7 articles about (1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine 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: 54.0%

: 66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9
adenine

: 288103-12-8
(1R,4S,5R)-methanesulfonic acid 3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl ester

: C₂₄H₂₇N₅O₃

: 288103-13-9
(1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 18h;
DOI:10.1021/jo000154x

Reference yield:

: 933-40-4
cycloxexanone dimethyl ketal

: 288103-13-9
(1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / TsOH / benzene / 0.5 h / Heating

2: 52 percent / n-BuLi / tetrahydrofuran / 2.5 h / -78 °C

3: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.17 h / 0 °C

4: 86 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

5: 54 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 18 h / 70 °C

With sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Condensation / 2: Ring cleavage / 3: Reduction / 4: Substitution / 5: Substitution;
DOI:10.1021/jo000154x

Reference yield:

: 288103-07-1
(-)-5-(benzyloxymethyl)-5-ethoxy-5H-furan-2-one

: 288103-13-9
(1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

Guidance literature:: Multi-step reaction with 6 steps

1: 50 percent / KMnO₄; cis-dicyclohexano-18-crown-6 / CH₂Cl₂ / 2.5 h / -40 °C

2: 86 percent / TsOH / benzene / 0.5 h / Heating

3: 52 percent / n-BuLi / tetrahydrofuran / 2.5 h / -78 °C

4: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.17 h / 0 °C

5: 86 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

6: 54 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 18 h / 70 °C

With sodium tetrahydroborate; potassium permanganate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; dicyclohexano-18-crown-6; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Oxidation / 2: Condensation / 3: Ring cleavage / 4: Reduction / 5: Substitution / 6: Substitution;
DOI:10.1021/jo000154x