5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine

Base Information

• Chemical Name: 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine
• CAS No.: 1401307-46-7
• Molecular Formula: C₂₄H₃₃N₅O₄Si
• Molecular Weight: 489.595
• Mol file: 1401307-46-7.mol

Synonyms:5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine

Chemical Property of 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine

There total 4 articles about 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine 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: 95.0%

ethynylbenzene-D5 (25837-46-1) + 1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione (120624-97-7) → 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D5)-1H-1,2,3-triazol-1-yl)thymidine (1401307-46-7)

Guidance literature:

With copper(ll) sulfate pentahydrate; water-d2; sodium L-ascorbate; In dichloromethane; at 20 ℃; for 8h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo301146j DOI:10.1021/jo301146j

Reference yield: 95.0%

→ 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D5)-1H-1,2,3-triazol-1-yl)thymidine (1401307-46-7)

Guidance literature:

Reference yield:

C17H21(2)H5Si (1401307-49-0) → 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D5)-1H-1,2,3-triazol-1-yl)thymidine (1401307-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / diethyl ether; tetrahydrofuran

2: copper(ll) sulfate pentahydrate; sodium L-ascorbate; water-d2 / dichloromethane / 8 h / 20 °C / Inert atmosphere

With copper(ll) sulfate pentahydrate; tetrabutyl ammonium fluoride; water-d2; sodium L-ascorbate; In tetrahydrofuran; diethyl ether; dichloromethane; 2: |Huisgen Cycloaddition;

DOI:10.1021/jo301146j DOI:10.1021/jo301146j

upstream raw materials:

ethynylbenzene-D5

1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione

bromobenzene-d5

C₁₇H₂₁⁽²⁾H₅Si