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

Base Information

• Chemical Name: 1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione
• CAS No.: 166769-33-1
• Molecular Formula: C₂₈H₂₅N₅O₅
• Molecular Weight: 511.537

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

Chemical Property of 1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione

There total 6 articles about 1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-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: 73.4%

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione (96253-10-0) → 1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione (166769-33-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 36h;

DOI:10.1016/j.tet.2010.12.054

Reference yield: 65.0%

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione (96253-10-0) → 1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione (166769-33-1) + 1-(2-azido-2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl)pyrimidine-2,4(1H,3H)-dione (1426142-28-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 130 ℃; for 5h; Inert atmosphere;

DOI:10.1002/hlca.201200285

Reference yield:

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione (110524-37-3) → 1-[3-azido-3-deoxy-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4-(1H,3H)-dione (166769-33-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium azide; sodium hydroxide; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2010.12.054

upstream raw materials:

trityl chloride

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

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

5'-O-trityluridine

Downstream raw materials:

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

3'-azido-2'-O-benzoyl-3'-deoxy-5'-O-(triphenylmethyl)uridine

3'-azido-3'-deoxy-5'-O-(triphenylmethyl)uridine

1-{(5aR,6R,8S,8aR)-5a,6,8,8a-tetrahydro-8-[(triphenylmethoxy)methyl]-4H-furo[3,4-b][1,2,3]triazolo[1,5-d][1,4]oxazin-6-yl}pyrimidine-2,4(1H,3H)-dione

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