1433369-48-2

Upstream product

• 89747-54-6 (3R,4R,5R)-4,5-dihydro-3,4-(O,O)-isopropylidene-5-mesyloxymethyl-2-(3H)-furanone 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 5336-08-3 D-Ribono-1,4-lactone 
• 532-20-7 D-Ribose 
• 5451-40-1 2,6 dichloropurine 
• 1320269-76-8 (3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 152006-17-2 2,3-O-isopropylidene-L-lyxono-1,4-lactone 
• 1006032-32-1 acetic acid 6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl ester 
• 1433368-95-6 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine 
• 1006032-31-0 C₂₄H₃₂O₄SeSi 
• 1006032-30-9 (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole 
• 1006032-29-6 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol 
• 1006364-60-8 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-L-lyxitol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Relevant academic research and scientific papers

Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar

The synthesis of a variety of chemically modified oligonucleotides requires the development of a practical synthetic method for its building block, i.e., nucleoside analogs. The one-pot Pummerer-like reaction using hypervalent iodine in combination with 6-chloropurine and an ‘armed’ 4-selenosugar bearing an electron-donating group at the 2-position gave the desired 4′-seleno-6-chloropurine derivative in higher yield as compared to the previous method using a ‘disarmed’ 4-selenosugar bearing an electron-withdrawing group at the 2-position. In addition, the use of 2,6-dichloropurine as a nucleobase transformable into guanine skeleton enabled an effective Pummerer-like reaction followed by isomerization to the desired N9 isomer under the acidic conditions. This Pummerer-like reaction between chlorinated purine bases and an ‘armed’ 4-selenosugar is advantageous because it affords 4′-selenopurine nucleosides in one-pot without the need for isolation of the unstable selenoxide derivative.

New RNA purine building blocks, 4'-selenopurine nucleosides: First synthesis and unusual mixture of sugar puckerings

Writer's blocks: The first synthesis of RNA purine building blocks, 4'-selenoadenosine and 4'-selenoguanosine was achieved from D-ribose by regioisomeric rearrangement, which was confirmed by X-ray crystallography. 4'-Selenoadenosine exists in an unusual mixture of north and south conformers in the solid state.