1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione
CAS No.:459448-78-3
Molecular Formula:C₂₉H₂₆ClN₅O₅
Molecular Weight:560.009
Hs Code.:

Synonyms:1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

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Technology Process of 1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

There total 8 articles about 1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-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: 60.0%

: 76-83-5
trityl chloride

: 459448-75-0
1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

: 459448-78-3
1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

Guidance literature:: With dmap; In pyridine;
DOI:10.1081/SCC-120003150

Reference yield:

: 13299-15-5
2-deoxy-D-glucose

: 459448-78-3
1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine

2: TMSOTf / acetonitrile / 3 h / 20 - 85 °C

3: 93 percent / NH₃ / methanol

4: 71 percent / HBF₄ / dimethylformamide

5: 80 percent / DMAP / pyridine / 32 h

6: 80 percent / NaN₃ / dimethylformamide / 4 h / 135 °C / Heating

7: 85 percent / aq. TFA / 4 h

8: 60 percent / DMAP / pyridine

With pyridine; dmap; tetrafluoroboric acid; sodium azide; trimethylsilyl trifluoromethanesulfonate; ammonia; trifluoroacetic acid; In pyridine; methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1081/SCC-120003150

Reference yield:

: 459448-63-6
5-Chloro-1-((2R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1H-pyrimidine-2,4-dione

: 459448-78-3
1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yl)-5-chloro-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 71 percent / HBF₄ / dimethylformamide

2: 80 percent / DMAP / pyridine / 32 h

3: 80 percent / NaN₃ / dimethylformamide / 4 h / 135 °C / Heating

4: 85 percent / aq. TFA / 4 h

5: 60 percent / DMAP / pyridine

With dmap; tetrafluoroboric acid; sodium azide; trifluoroacetic acid; In pyridine; N,N-dimethyl-formamide;
DOI:10.1081/SCC-120003150