(-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene

Base Information

Chemical Name:(-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene
CAS No.:902455-29-2
Molecular Formula:C₃₄H₃₃N₅O₃
Molecular Weight:559.668
Hs Code.:

Synonyms:(-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene

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Chemical Property of (-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene

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Technology Process of (-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene

There total 7 articles about (-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene 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: 78.0%

: 902455-28-1
(+)-(1S,2S,3R)-2,3-O-isopropylidene-3-(2-triphenylmetoxyethyl)-4-cyclopentenyl p-toluenesulfonate

: 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

: 902455-29-2
(-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene

: 7-[2,2-dimethyl-6a-(2-trityloxy-ethyl)-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-7H-purin-6-ylamine

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 12h;
DOI:10.1016/j.tet.2006.04.042

Reference yield:

: (4R,5S)-5-((S)-1-Hydroxy-allyl)-2,2-dimethyl-4-vinyl-[1,3]dioxolane-4-carbaldehyde

: 902455-29-2
(-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene

Guidance literature:: Multi-step reaction with 6 steps

1.1: second generation Grubbs catalyst / CH₂Cl₂ / 5 h / 20 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

2.2: 826 mg / tetrahydrofuran / 12 h / 20 °C

3.1: borane-dimethyl sulfide; 2-methyl-2-butene / tetrahydrofuran / 0 - 20 °C

3.2: 71 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: 76 percent / 4-(dimethylamino)pyridine; pyridine / 24 h / 20 °C

5.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

6.1: 78 percent / 18-crown-6; K₂CO₃ / dimethylformamide / 12 h / 80 °C

With pyridine; dmap; 2-methyl-but-2-ene; 18-crown-6 ether; dimethylsulfide borane complex; potassium tert-butylate; potassium carbonate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.2: Wittig reaction;
DOI:10.1016/j.tet.2006.04.042

Reference yield:

: 474329-16-3
(-)-(1S)-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl]prop-2-en-1-ol

: 902455-29-2
(-)-(3R,4S,5S)-3,4-O-isopropylidene-3-(2-triphenylmethoxyethyl)-5-(adenin-9-yl)cyclopentene

Guidance literature:: Multi-step reaction with 7 steps

1.1: TEMPO; tetrabutylammonium chloride; N-chlorosuccinimide / NaHCO₃; K₂CO₃ / CH₂Cl₂; H₂O / 3 h / 20 °C / pH 8.6

2.1: second generation Grubbs catalyst / CH₂Cl₂ / 5 h / 20 °C

3.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

3.2: 826 mg / tetrahydrofuran / 12 h / 20 °C

4.1: borane-dimethyl sulfide; 2-methyl-2-butene / tetrahydrofuran / 0 - 20 °C

4.2: 71 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

5.1: 76 percent / 4-(dimethylamino)pyridine; pyridine / 24 h / 20 °C

6.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

7.1: 78 percent / 18-crown-6; K₂CO₃ / dimethylformamide / 12 h / 80 °C

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; 2-methyl-but-2-ene; 18-crown-6 ether; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl-ammonium chloride; potassium carbonate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 3.2: Wittig reaction;
DOI:10.1016/j.tet.2006.04.042