(2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

Base Information

Chemical Name:(2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate
CAS No.:1274677-37-0
Molecular Formula:C₃₀H₂₇N₅O₆
Molecular Weight:553.574
Hs Code.:

Synonyms:(2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

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Chemical Property of (2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

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Technology Process of (2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

There total 6 articles about (2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate 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: 90.0%

: 166769-33-1
1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione

: 108-24-7
acetic anhydride

: 1274677-37-0
(2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

Guidance literature:: With pyridine; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2010.12.054

Reference yield:

: 96253-10-0
1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione

: 1274677-37-0
(2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium azide / N,N-dimethyl-formamide / 36 h / 80 °C

2: pyridine / 3 h / 20 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2010.12.054

Reference yield:

: 110524-37-3
1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione

: 1274677-37-0
(2R,3S,4R,5S)-4-azido-2-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)-5-(trityloxymethyl)-tetrahydrofuran-3-ylacetate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydroxide / water; acetone / 18 h / 20 °C

2: sodium azide / N,N-dimethyl-formamide / 36 h / 80 °C

3: pyridine / 3 h / 20 °C

With pyridine; sodium azide; sodium hydroxide; In water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2010.12.054