Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester
CAS No.:314080-73-4
Molecular Formula:C₁₇H₁₆N₂O₇
Molecular Weight:360.323
Hs Code.:

Synonyms:Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

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Chemical Property of Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

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Technology Process of Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

There total 6 articles about Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl 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: 95.0%

: 532-32-1
sodium benzoate

: 314080-72-3
Toluene-4-sulfonic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

: 314080-73-4
Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

Guidance literature:: In N,N-dimethyl-formamide; at 90 ℃; for 3h;
DOI:10.1016/S0960-894X(00)00434-0

Reference yield:

: 1-(6,6-bis-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

: 314080-73-4
Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 60 percent / DMAP / CH₂Cl₂ / 6 h / 20 °C

2: 97 percent / K₂CO₃ / dimethylformamide / 20 °C

3: 100 percent / 80 percent aq. AcOH / 6 h / Heating

4: NaH / dimethylformamide / 1 h / 20 °C

5: 95 percent / aq. cerium ammonium nitrate / acetonitrile / 18 h / 20 °C

6: 95 percent / dimethylformamide / 3 h / 90 °C

With dmap; ammonium cerium(IV) nitrate; sodium hydride; potassium carbonate; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Tosylation / 2: Alkylation / 3: Hydrolysis / 4: Cyclization / 5: oxidative cleavage / 6: Substitution;
DOI:10.1016/S0960-894X(00)00434-0

Reference yield:

: 314080-70-1
Toluene-4-sulfonic acid (1R,3R,4R,5S)-4-hydroxy-3-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

: 314080-73-4
Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / aq. cerium ammonium nitrate / acetonitrile / 18 h / 20 °C

2: 95 percent / dimethylformamide / 3 h / 90 °C

With ammonium cerium(IV) nitrate; In N,N-dimethyl-formamide; acetonitrile; 1: oxidative cleavage / 2: Substitution;
DOI:10.1016/S0960-894X(00)00434-0