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

Base Information

Chemical Name:1-[3,7-anhydro-5-azido-8-O-benzyl-5-deoxy-2-O-(2,2-dimethylpropionyl)-D-erythro-α-D-allo-octofuranosyl]-1H-3-(benzyloxymethyl)-5-iodopyrimidine-2,4-dione
CAS No.:277317-34-7
Molecular Formula:C₃₂H₃₆IN₅O₉
Molecular Weight:761.57
Hs Code.:

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

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

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

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

There total 4 articles about 1-[3,7-anhydro-5-azido-8-O-benzyl-5-deoxy-2-O-(2,2-dimethylpropionyl)-D-erythro-α-D-allo-octofuranosyl]-1H-3-(benzyloxymethyl)-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: 85.0%

: 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

: 277317-34-7
1-[3,7-anhydro-5-azido-8-O-benzyl-5-deoxy-2-O-(2,2-dimethylpropionyl)-D-erythro-α-D-allo-octofuranosyl]-1H-3-(benzyloxymethyl)-5-iodopyrimidine-2,4-dione

Guidance literature:: With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ol005696f

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 277317-34-7
1-[3,7-anhydro-5-azido-8-O-benzyl-5-deoxy-2-O-(2,2-dimethylpropionyl)-D-erythro-α-D-allo-octofuranosyl]-1H-3-(benzyloxymethyl)-5-iodopyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / BEMP / tetrahydrofuran / 45 h / 0 °C

2: 85 percent / HCl; Na(CN)BH₃; molecular sieves 3 Angstroem / tetrahydrofuran; diethyl ether

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In tetrahydrofuran; diethyl ether; 1: Addition / 2: Hydrolysis;
DOI:10.1021/ol005696f

Reference yield:

: 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

: 277317-34-7
1-[3,7-anhydro-5-azido-8-O-benzyl-5-deoxy-2-O-(2,2-dimethylpropionyl)-D-erythro-α-D-allo-octofuranosyl]-1H-3-(benzyloxymethyl)-5-iodopyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 65 percent / N-iodosuccinimide; TfOH / 1,2-dichloro-ethane / 2.5 h / 20 °C

2: 95 percent / BEMP / tetrahydrofuran / 45 h / 0 °C

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

With hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; sodium cyanoborohydride; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In tetrahydrofuran; diethyl ether; 1,2-dichloro-ethane; 1: Substitution / 2: Addition / 3: Hydrolysis;
DOI:10.1021/ol005696f