(+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil

Base Information

Chemical Name:(+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil
CAS No.:479035-98-8
Molecular Formula:C₂₅H₂₇FN₂O₃SSi
Molecular Weight:482.651
Hs Code.:

Synonyms:(+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil

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Chemical Property of (+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil

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Technology Process of (+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil

There total 12 articles about (+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil 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: 68.0%

: 479035-94-4
(-)-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]uracil

: 479035-98-8
(+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil

Guidance literature:: (-)-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]uracil; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.5h;

With pyridine; In dichloromethane; at 20 ℃; for 2h; Further stages.;
DOI:10.1021/jm020376i

Reference yield:

: 212954-52-4
(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one

: 479035-98-8
(+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil

Guidance literature:: Multi-step reaction with 12 steps

1.1: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 3 h

2.1: aq. NaOH / ethanol / 2 h / 20 °C

3.1: dimethylsulfoxide / 1 h

4.1: 82 percent / I₂; Ph₃P; imidazole / toluene / 4 h / 60 °C

5.1: 91 percent / dimethylformamide / 8 h / 20 °C

6.1: DIBAL-H / hexane; toluene / 1 h / -78 °C

7.1: Ac₂O; DMSO / 24 h / 20 °C

8.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

8.2: TMSCl / tetrahydrofuran / 20 °C

8.3: 74 percent / tetrahydrofuran / 1 h / -78 °C

9.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

10.1: TEA; 4-DMAP / CH₂Cl₂ / 3 h / 20 °C

11.1: HMDS / acetonitrile / 5 h / Heating

11.2: 48 percent / TMSOTf / acetonitrile / 16 h / 20 °C

12.1: mCPBA / CH₂Cl₂ / 0.5 h / -78 °C

12.2: 68 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; TEA; hydrogen; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; 5percent Pd/C; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Mitsunobu reaction / 7.1: Moffatt-type oxidation;
DOI:10.1021/jm020376i

Reference yield:

: 398133-29-4
(2R,4R)-(-)-4-tert-butyldiphenylsilyloxymethyl-2-fluoro-γ-butyrolactone

: 479035-98-8
(+)-1-[(1S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-L-ribofuranosyl]uracil

Guidance literature:: Multi-step reaction with 11 steps

1.1: aq. NaOH / ethanol / 2 h / 20 °C

2.1: dimethylsulfoxide / 1 h

3.1: 82 percent / I₂; Ph₃P; imidazole / toluene / 4 h / 60 °C

4.1: 91 percent / dimethylformamide / 8 h / 20 °C

5.1: DIBAL-H / hexane; toluene / 1 h / -78 °C

6.1: Ac₂O; DMSO / 24 h / 20 °C

7.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

7.2: TMSCl / tetrahydrofuran / 20 °C

7.3: 74 percent / tetrahydrofuran / 1 h / -78 °C

8.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

9.1: TEA; 4-DMAP / CH₂Cl₂ / 3 h / 20 °C

10.1: HMDS / acetonitrile / 5 h / Heating

10.2: 48 percent / TMSOTf / acetonitrile / 16 h / 20 °C

11.1: mCPBA / CH₂Cl₂ / 0.5 h / -78 °C

11.2: 68 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; TEA; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Mitsunobu reaction / 6.1: Moffatt-type oxidation;
DOI:10.1021/jm020376i