(2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

Base Information

Chemical Name:(2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide
CAS No.:616894-66-7
Molecular Formula:C₂₅H₂₉N₃O₈
Molecular Weight:499.521
Hs Code.:

(2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

Synonyms:(2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

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Chemical Property of (2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

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Technology Process of (2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

There total 3 articles about (2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide 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: 59.0%

: 107-11-9,30551-89-4
1-amino-2-propene

: 616894-53-2
1-{(3aR,4R,6R,6aR)-6-[(2S,3R)-3-(Indole-1-carbonyl)-oxiranyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-3-(4-methoxy-benzyl)-1H-pyrimidine-2,4-dione

: 616894-66-7
(2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

: (2S,3R)-N-Allyl-2-allylamino-3-hydroxy-3-{(3aR,4R,6R,6aR)-6-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-propionamide

Guidance literature:: In tetrahydrofuran; at 50 ℃; for 12h;
DOI:10.1021/ol0355074

Reference yield:

: 121845-98-5
(3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde

: 616894-66-7
(2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / aq. NaOH / CH₂Cl₂ / 2.5 h

2: 76 percent / DDQ / benzene / 24 h / Heating

3: 59 percent / tetrahydrofuran / 12 h / 50 °C

With sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ol0355074

Reference yield:

: 616894-52-1
1-{(3aR,4R,6R,6aR)-6-[(2S,3R)-3-(2,3-Dihydro-indole-1-carbonyl)-oxiranyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-3-(4-methoxy-benzyl)-1H-pyrimidine-2,4-dione

: 616894-66-7
(2R,3S)-3-{(3aR,4R,6R,6aR)-6-[3-(4-Methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-oxirane-2-carboxylic acid allylamide

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / DDQ / benzene / 24 h / Heating

2: 59 percent / tetrahydrofuran / 12 h / 50 °C

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; benzene;
DOI:10.1021/ol0355074