9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine

Base Information

Chemical Name:9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine
CAS No.:1391597-17-3
Molecular Formula:C₂₃H₂₇N₅O₃
Molecular Weight:421.499
Hs Code.:

Synonyms:9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine

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Chemical Property of 9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine

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Technology Process of 9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine

There total 5 articles about 9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine 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: 47.0%

: 1391597-16-2
9-(((2R,3S,4R,5S)-5-allyl-4-(allyloxy)-3-(benzyloxy)tetrahydrofuran-2-yl)methyl)-9H-purin-6-amine

: 1391597-17-3
9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In benzene; for 6h; Inert atmosphere; Reflux;
DOI:10.1021/ol301851q

Reference yield:

: 34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1
3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 1391597-17-3
9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine

Guidance literature:: Multi-step reaction with 5 steps

1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane / 12.5 h / 20 °C

2: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

3: pyridine / dichloromethane / 1 h / 0 °C

4: 18-crown-6 ether; potassium carbonate / 14 h / Reflux

5: Hoveyda-Grubbs catalyst second generation / benzene / 6 h / Inert atmosphere; Reflux

With pyridine; Hoveyda-Grubbs catalyst second generation; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutylammomium bromide; potassium carbonate; sodium hydroxide; In dichloromethane; benzene;
DOI:10.1021/ol301851q

Reference yield:

: 167777-14-2
(3aR,5R,6S,6aR)-5-(allyloxymethyl)-6-(benzyloxy)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: 1391597-17-3
9-(((2R,3S,3aR,8aS)-3-(benzyloxy)-2,3,3a,5,8,8a-hexahydrofuro[3,2-b]oxepin-2-yl)methyl)-N,N-dimethyl-9H-purin-6-amine

Guidance literature:: Multi-step reaction with 4 steps

1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

2: pyridine / dichloromethane / 1 h / 0 °C

3: 18-crown-6 ether; potassium carbonate / 14 h / Reflux

4: Hoveyda-Grubbs catalyst second generation / benzene / 6 h / Inert atmosphere; Reflux

With pyridine; Hoveyda-Grubbs catalyst second generation; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium carbonate; In dichloromethane; benzene;
DOI:10.1021/ol301851q