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

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Chemical Name: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
CAS No.:314080-72-3
Molecular Formula:C₁₇H₁₈N₂O₈S
Molecular Weight:410.405
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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%

: 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

: 314080-72-3
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

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile; at 20 ℃; for 18h;
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

: 314080-72-3
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

Guidance literature:: Multi-step reaction with 5 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

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;
DOI:10.1016/S0960-894X(00)00434-0

Reference yield:

: 314080-66-5
C₂₇H₃₀N₂O₁₁S₂

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / K₂CO₃ / dimethylformamide / 20 °C

2: 100 percent / 80 percent aq. AcOH / 6 h / Heating

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

4: 95 percent / aq. cerium ammonium nitrate / acetonitrile / 18 h / 20 °C

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