1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

Base Information

Chemical Name:1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione
CAS No.:277317-30-3
Molecular Formula:C₂₄H₂₆IN₅O₈
Molecular Weight:639.404
Hs Code.:

1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

Synonyms:1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

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Chemical Property of 1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

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Technology Process of 1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

There total 1 articles about 1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-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: 65.0%

: 154706-36-2
2,2-Dimethyl-propionic acid (2S,4aR,5aR,6R,7R,8aR,9R,9aR)-9-azido-2-phenyl-7-phenylsulfanyl-octahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-6-yl ester

: 10457-14-4
O,O'-bis-(trimethylsilyl)uracil

: 2,2-Dimethyl-propionic acid (2S,4aR,5aR,6R,7R,8aR,9S,9aR)-9-azido-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-octahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-6-yl ester

: 277317-30-3
1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at 20 ℃; for 2.5h;
DOI:10.1021/ol005696f

Reference yield: 95.0%

: 3587-60-8
Benzyloxymethyl chloride

: 277317-30-3
1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

: 2,2-Dimethyl-propionic acid (2S,4aR,5aR,6R,7R,8aR,9S,9aR)-9-azido-7-(3-benzyloxymethyl-5-iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-octahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-6-yl ester

Guidance literature:: With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In tetrahydrofuran; at 0 ℃; for 45h;
DOI:10.1021/ol005696f

Reference yield:

: 277317-30-3
1-[3,7-anhydro-5-azido-5-deoxy-2-O-(2,2-dimethylpropionyl)-6,8-O-(phenylmethylene)-D-erythro-α-D-allo-octofuranosyl]-1H,3H-5-iodopyrimidine-2,4-dione

: 277317-44-9
7-(3-benzoyl-ureido)-6-[6-carboxy-3-(2,2-dimethyl-propionyloxy)-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-3-(2,2-dimethyl-propionyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,2-b]pyran-5-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / BEMP / tetrahydrofuran / 45 h / 0 °C

2.1: 85 percent / HCl; Na(CN)BH₃; molecular sieves 3 Angstroem / tetrahydrofuran; diethyl ether

3.1: 78 percent / N-iodosuccinimide; TfOH; molecular sieves 3 Angstroem / 1,2-dichloro-ethane / 0.67 h / 20 °C

4.1: 80 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

5.1: H₂ / Lindlar catalyst / tetrahydrofuran / 2 h / 20 °C

6.1: 67 percent / CH₂Cl₂ / 2 h / 20 °C

7.1: 84 percent / H₂ / Pd(OH)2/C / ethyl acetate; ethanol / 2 h / 20 °C

8.1: PhI(OAc)2; TEMPO; NaHCO₃ / acetonitrile; H₂O / 4 h / 20 °C

8.2: 58 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-iodo-succinimide; trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; palladium dihydroxide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; acetonitrile; 1.1: Addition / 2.1: Hydrolysis / 3.1: Glycosylation / 4.1: Dehalogenation / 5.1: Hydrogenolysis / 6.1: Acylation / 7.1: Hydrogenolysis / 8.1: Oxidation / 8.2: Oxidation;
DOI:10.1021/ol005696f