(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione
CAS No.:865838-14-8
Molecular Formula:C₃₉H₃₃FN₂O₆
Molecular Weight:644.699
Hs Code.:

Synonyms:(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

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Chemical Property of (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

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Technology Process of (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

There total 12 articles about (3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-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: 75.0%

: 2775-87-3
3-N-benzoyluracil

: 805245-42-5
(3aS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

: 865838-14-8
(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 15h;

Reference yield:

: 54503-64-9,54503-65-0
2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

: 865838-14-8
(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 11 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 7 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

2.2: 1 h / -78 - 20 °C

3.1: tetrahydrofuran / 1 h / -78 °C

4.1: tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride / dichloromethane / 48 h / 20 °C

5.1: dipyridinium dichromate / molecular sieve / N,N-dimethyl-formamide / 48 h / 20 °C

6.1: pyridine; iodine / dichloromethane / 6 h / 0 - 20 °C

7.1: sodium tetrahydroborate; cerium(III) chloride / methanol; water / 1 h / 0 °C

8.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

9.1: n-butyllithium; N-fluorobis(benzenesulfon)imide / tetrahydrofuran; hexane / 1 h / -78 °C

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

11.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 0 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; dimethyl sulfoxide; N-fluorobis(benzenesulfon)imide; triphenylphosphine; diethylazodicarboxylate; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; molecular sieve; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Wittig Reaction / 2.1: Swern Oxidation / 3.1: Grignard Reaction;

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 865838-14-8
(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 12 steps

1.1: pyridine / 20 h / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C

2.2: 7 h / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

3.2: 1 h / -78 - 20 °C

4.1: tetrahydrofuran / 1 h / -78 °C

5.1: tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride / dichloromethane / 48 h / 20 °C

6.1: dipyridinium dichromate / molecular sieve / N,N-dimethyl-formamide / 48 h / 20 °C

7.1: pyridine; iodine / dichloromethane / 6 h / 0 - 20 °C

8.1: sodium tetrahydroborate; cerium(III) chloride / methanol; water / 1 h / 0 °C

9.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

10.1: n-butyllithium; N-fluorobis(benzenesulfon)imide / tetrahydrofuran; hexane / 1 h / -78 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

12.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 0 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; dimethyl sulfoxide; N-fluorobis(benzenesulfon)imide; triphenylphosphine; diethylazodicarboxylate; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; molecular sieve; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Wittig Reaction / 3.1: Swern Oxidation / 4.1: Grignard Reaction;