2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine

Base Information

• Chemical Name: 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine
• CAS No.: 188117-96-6
• Molecular Formula: C₃₀H₅₆N₄O₄Si₃
• Molecular Weight: 621.056
• Mol file: 188117-96-6.mol

Synonyms:2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine

Chemical Property of 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine

There total 1 articles about 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine 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:

tri-n-butyl(vinyl)tin (7486-35-3) + 6-chloro-9-(2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-9H-purine (84765-96-8) → tributyltin chloride (1461-22-9) + 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine (188117-96-6)

Guidance literature:

With potassium fluoride; bis(triphenylphosphine)palladium(II)-chloride; Yield given. Multistep reaction; 1.) dichloroethane, reflux, 2.5 h, 2.) methanol, ambient temperature, 15 min;

DOI:10.1016/S0040-4020(96)01089-7

Reference yield:

iodobenzene (591-50-4) + 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine (188117-96-6) → (E)-6-(phenylethenyl)-9-(O,O,O-tris(tert-butyldimethylsilyl)-α-D-ribofuranosyl)-9H-purine (646522-20-5)

Guidance literature:

With palladium diacetate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60 ℃; for 15h;

DOI:10.1016/S0960-894X(03)00011-8

Reference yield:

2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-vinylnebularine (188117-96-6) → trans-6-styryl-9β-D-ribofuranosyl-9H-purine

Guidance literature:

Multi-step reaction with 2 steps

1: palladium acetate; ethyldiisopropylamine / dimethylformamide / 15 h / 60 °C

2: 47 percent / TBAF / tetrahydrofuran / 16 h / 20 °C

With tetrabutyl ammonium fluoride; palladium diacetate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Heck reaction;

DOI:10.1016/S0960-894X(03)00011-8

upstream raw materials:

tri-n-butyl(vinyl)tin

6-chloro-9-(2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-9H-purine

Downstream raw materials:

(E)-6-(phenylethenyl)-9-(O,O,O-tris(tert-butyldimethylsilyl)-α-D-ribofuranosyl)-9H-purine