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

Base Information

• Chemical Name: 1-[(2R,3R,4S,5R)-3-Hydroxy-4-(2-hydroxy-ethylsulfanyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 202259-88-9
• Molecular Formula: C₃₀H₃₀N₂O₆S
• Molecular Weight: 546.644

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

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

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

There total 2 articles about 1-[(2R,3R,4S,5R)-3-Hydroxy-4-(2-hydroxy-ethylsulfanyl)-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: 96.0%

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,3R,4S,5R)-3-Hydroxy-4-(2-hydroxy-ethylsulfanyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (202259-88-9)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 2h; 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) + 2-hydroxyethanethiol (60-24-2) → 1-[(2R,3R,4S,5R)-3-Hydroxy-4-(2-hydroxy-ethylsulfanyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (202259-88-9) + 1-[(2R,3R,4S,5R)-4-Hydroxy-3-(2-hydroxy-ethylsulfanyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:

With N,N,N',N'-tetramethylguanidine; Multistep reaction. Title compound not separated from byproducts; 1.) DMF, 70 deg C, 10 min, 2.) DMF, 70 deg C, 2 h;

DOI:10.1021/jo9705576

Reference yield: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1-[(2R,3R,4S,5R)-3-Hydroxy-4-(2-hydroxy-ethylsulfanyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (202259-88-9) → 1-[3-S-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)-3-thio-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4(1H,3H)-dione (202260-05-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 8h; Ambient temperature;

DOI:10.1021/jo9705576

upstream raw materials:

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

2-hydroxyethanethiol

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

Downstream raw materials:

1-[3-S-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)-3-thio-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4(1H,3H)-dione

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

1-((2R,5R)-4-Ethenesulfonyl-5-trityloxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione

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

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