1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 202260-08-0
• Molecular Formula: C₃₀H₂₉N₅O₇S
• Molecular Weight: 603.656

Synonyms:1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Chemical Property of 1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

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Technology Process of 1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

There total 4 articles about 1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-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: 87.0%

1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethylsulfanyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (202260-07-9) → 1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (202260-08-0)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In methanol; Ambient temperature;

DOI:10.1021/jo9705576

Reference yield:

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione (96253-10-0) → 1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (202260-08-0)

Guidance literature:

Multi-step reaction with 4 steps

2: 70 percent / LiN₃ / dimethylformamide / 3 h / 140 °C

3: 95 percent / NaOH / ethanol; H₂O / 2 h / Ambient temperature

4: 87 percent / magnesium monoperphthalate / methanol / Ambient temperature

With sodium hydroxide; lithium azide; magnesium monoperoxyphthalate hexahydrate; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo9705576

Reference yield:

Benzoic acid 2-((2R,3R,3aR,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-ylsulfanyl)-ethyl ester (202259-89-0) → 1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (202260-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / LiN₃ / dimethylformamide / 3 h / 140 °C

2: 95 percent / NaOH / ethanol; H₂O / 2 h / Ambient temperature

3: 87 percent / magnesium monoperphthalate / methanol / Ambient temperature

With sodium hydroxide; lithium azide; magnesium monoperoxyphthalate hexahydrate; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo9705576

upstream raw materials:

1-[(2R,3S,4S,5R)-3-Azido-4-(2-hydroxy-ethylsulfanyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione

Benzoic acid 2-((2R,3R,3aR,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-ylsulfanyl)-ethyl ester

Benzoic acid 2-[(2R,3S,4S,5R)-4-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-ylsulfanyl]-ethyl ester

Downstream raw materials:

1-((1R,3R,3aS,7aS)-4,4-Dioxo-3-trityloxymethyl-octahydro-2-oxa-4λ⁶-thia-7-aza-inden-1-yl)-1H-pyrimidine-2,4-dione

1-[(2R,3S,4S,5R)-3-Amino-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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