(-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:(-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:917377-34-5
Molecular Formula:C₃₃H₃₅FN₂O₄SSi
Molecular Weight:602.802
Hs Code.:

Synonyms:(-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of (-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of (-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 7 articles about (-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione 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: 66.0%

: 917377-32-3
(+)-(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-ol

: 4330-20-5
N-3-benzoylthymine

: 917377-34-5
(-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.bmc.2006.09.066

Reference yield:

: 917377-29-8
benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl ester

: 917377-34-5
(-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / NaOMe / CH₂Cl₂; methanol / 4 h / 20 °C

2: 88 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 5 h / 60 °C

3: 92 percent / NaOMe / CH₂Cl₂; methanol / 20 °C

4: 66 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 20 °C

With sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 2: Mitsunobu reaction / 4: Mitsunobu reaction;
DOI:10.1016/j.bmc.2006.09.066

Reference yield:

: 917377-27-6
benzoic acid (+)-(3S,4S,5R)-4-benzyloxy-5-(tert-butyldiphenylsilanyloxymethyl)tetrahydrothien-3-yl ester

: 917377-34-5
(-)-3-benzoyl-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / boron trichloride / CH₂Cl₂ / 0.67 h / -78 °C

2: 88 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0.5 h / -10 °C

3: 96 percent / NaOMe / CH₂Cl₂; methanol / 4 h / 20 °C

4: 88 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 5 h / 60 °C

5: 92 percent / NaOMe / CH₂Cl₂; methanol / 20 °C

6: 66 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 20 °C

With diethylamino-sulfur trifluoride; sodium methylate; boron trichloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 4: Mitsunobu reaction / 6: Mitsunobu reaction;
DOI:10.1016/j.bmc.2006.09.066