(+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

Base Information

Chemical Name:(+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine
CAS No.:132150-29-9
Molecular Formula:C₂₅H₂₇ClN₄O₄
Molecular Weight:482.967
Hs Code.:

Synonyms:(+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

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Chemical Property of (+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

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Technology Process of (+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

There total 7 articles about (+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine 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: 42.0%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 132150-28-8
(1R,2S,5R)-5-Amino-3,5-bis-benzyloxymethyl-cyclopent-3-ene-1,2-diol

: 132150-29-9
(+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

Guidance literature:: With triethylamine; In butan-1-ol; at 145 ℃; for 60h;
DOI:10.1016/S0040-4039(00)98007-9 DOI:10.1021/jo00074a030

Reference yield:

: 89291-75-8,117307-62-7
(3aR*,6aR*)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

: 132150-29-9
(+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -65 deg C, 3 min, 2.) 10 min

2: 1.) 2 N NH₃, BF₃*Et₂O, 2.) 50percent aq. CF₃COOH / 1.) CHCl₃, r.t., 16 h, 2.) r.t., 1.5 h

3: 99 percent / H₂ / Lindlar catalyst / methanol / 2 h

4: 42 percent / Et₃N / butan-1-ol / 60 h / 145 °C

With ammonium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; triethylamine; trifluoroacetic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; butan-1-ol;
DOI:10.1021/jo00074a030

Reference yield:

: 66222-28-4
(benzyloxymethyl)tributylstannane

: 132150-29-9
(+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -65 deg C, 3 min, 2.) 10 min

2: 1.) 2 N NH₃, BF₃*Et₂O, 2.) 50percent aq. CF₃COOH / 1.) CHCl₃, r.t., 16 h, 2.) r.t., 1.5 h

3: 99 percent / H₂ / Lindlar catalyst / methanol / 2 h

4: 42 percent / Et₃N / butan-1-ol / 60 h / 145 °C

With ammonium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; triethylamine; trifluoroacetic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; butan-1-ol;
DOI:10.1021/jo00074a030