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

Base Information

• Chemical Name: 1-[2-azido-2-deoxy-3-O-(prop-2-yn-1-yl)-5-O-(triphenylmethyl)-β-D-xylofuranosyl]pyrimidine-2,4(1H,3H)-dione
• CAS No.: 1426142-40-6
• Molecular Formula: C₃₁H₂₇N₅O₅
• Molecular Weight: 549.586
• Mol file: 1426142-40-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 1-[2-azido-2-deoxy-3-O-(prop-2-yn-1-yl)-5-O-(triphenylmethyl)-β-D-xylofuranosyl]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: 70.0%

1-(2-azido-2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl)pyrimidine-2,4(1H,3H)-dione (1426142-28-0) + propargyl bromide (106-96-7) → 1-[2-azido-2-deoxy-3-O-(prop-2-yn-1-yl)-5-O-(triphenylmethyl)-β-D-xylofuranosyl]pyrimidine-2,4(1H,3H)-dione (1426142-40-6)

Guidance literature:

1-(2-azido-2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl)pyrimidine-2,4(1H,3H)-dione; With sodium hydride; In tetrahydrofuran; mineral oil; for 0.5h; Inert atmosphere; Cooling with ice;

propargyl bromide; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.833333h; chemoselective reaction; Inert atmosphere; Sonication;

DOI:10.1002/hlca.201200285

Reference yield:

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione (96253-10-0) → 1-[2-azido-2-deoxy-3-O-(prop-2-yn-1-yl)-5-O-(triphenylmethyl)-β-D-xylofuranosyl]pyrimidine-2,4(1H,3H)-dione (1426142-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium azide / N,N-dimethyl-formamide / 5 h / 130 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / Inert atmosphere; Cooling with ice

2.2: 0.83 h / 20 °C / Inert atmosphere; Sonication

With sodium azide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/hlca.201200285

Reference yield: 87.0%

1-[2-azido-2-deoxy-3-O-(prop-2-yn-1-yl)-5-O-(triphenylmethyl)-β-D-xylofuranosyl]pyrimidine-2,4(1H,3H)-dione (1426142-40-6) → 1-{(5aR,6R,8R,8aR)-5a,6,8,8a-tetrahydro-6-[(triphenylmethoxy)methyl]-4H-furo[3,4-b][1,2,3]triazolo[1,5-d][1,4]oxazin-8-yl}pyrimidine-2,4(1H,3H)-dione (1426142-41-7)

Guidance literature:

In toluene; for 24h; Inert atmosphere; Reflux;

DOI:10.1002/hlca.201200285

upstream raw materials:

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

propargyl bromide

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

Downstream raw materials:

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

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