[(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

Base Information

Chemical Name:[(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester
CAS No.:181256-77-9
Molecular Formula:C₃₂H₃₃N₂O₈P
Molecular Weight:604.596
Hs Code.:

Synonyms:[(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

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Chemical Property of [(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

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Technology Process of [(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

There total 5 articles about [(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester 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: 79.0%

: 181256-76-8
[(2R,3R,4R,5R)-3,4-Dihydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-5-trityloxymethyl-tetrahydro-furan-3-yl]-phosphonic acid diethyl ester

: 181256-77-9
[(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

Guidance literature:: With trifluoromethane sulfonyl chloride; 4-pyrrolidin-1-ylpyridine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/0040-4020(96)00684-9

Reference yield:

: 76-83-5
trityl chloride

: 181256-77-9
[(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / AgNO₃, pyridine / tetrahydrofuran / Ambient temperature

2: 1.) LHMDS / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 0 deg C, 2 h

3: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) RT, 1h

4: 79 percent / triflyl chloride, 4-pyrrolidinopyridine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; trifluoromethane sulfonyl chloride; tetrabutyl ammonium fluoride; 4-pyrrolidin-1-ylpyridine; silver nitrate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4020(96)00684-9

Reference yield:

: 1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

: 181256-77-9
[(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / AgNO₃, pyridine / tetrahydrofuran / Ambient temperature

2: 1.) LHMDS / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 0 deg C, 2 h

3: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) RT, 1h

4: 79 percent / triflyl chloride, 4-pyrrolidinopyridine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; trifluoromethane sulfonyl chloride; tetrabutyl ammonium fluoride; 4-pyrrolidin-1-ylpyridine; silver nitrate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4020(96)00684-9