Nucleosides. LXV. Synthesis of New Pteridine–N8–Nucleosides
A general synthetic approach to various isoxanthopterin‐nucleosides starting from 6‐methyl‐2‐methylthio‐4(3H), 7(8H)‐pterdinedione (1) has been developed. Ribosylation with 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐d‐ribofuranose via the silyl‐method led to 2 and reaction with 1‐chloro‐2‐deoxy‐3,5‐di‐O‐p‐toluoyl‐α‐d‐ribofuranose using the DBU‐method afforded 28. Protection of the amide function at O4 by benzylation to 5 and by a Mitsunobu reaction with 2‐(4‐nitrophenyl)ethanol to 29 gave soluble intermediates which can be oxidized to the corresponding 2‐methylsulfonyl derivatives 8 and 30, respectively. Nucleophilic displacement reactions of the highly reactive 2‐methylsulfonyl functions by various amines proceeded under mild conditions to isoxanthopterin‐N8‐ribo‐ (11–17) and 2′‐deoxyribomucleosides (31–33). Debenzylation can be achieve by Pd‐catalyzed hydrogenation (9 to 19) and cleavage of the npe‐protecting group (31, 32 to 34, 35) works well with DBU by β‐elimination. #See Ref. 1. †In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.
C(2)-Functionalization of pyrimidin-4(3H)-one derivatives in the synthesis of its biologically active derivatives
Different approaches to the formation of biologically active isocytosine, uracil, and 2-thiouracil derivatives based on the C(2)-regioselective functionalization of pyrimidin-4(3H)one framework were considered.
“ PARTIALLY-ACTIVATED ” FLUX RESIDUE IMPACTS ON ELECTRONIC ASSEMBLY RELIABILITIES
The reliabilities of the flux residue of electronic assemblies and semiconductor packages are attracting more and more attention with the adoption of no-clean fluxes by majority of the industry. In recent years, the concern of “partiallyactivated” flux residue and their influence on reliability have been significantly raised due to the miniaturization along with high density design trend, selective soldering process adoption, and the expanded use of pallets in wave soldering process. When flux residue becomes trapped under low stand-off devices, pallets or unsoldered areas (e.g. selective process), it may contain unevaporated solvent, “live” activators and metal complex intermediates with different chemical composition and concentration levels depending on the thermal profiles. These partially-activated residues can directly impact the corrosion, surface insulation and electrochemical migration of the final assembly. In this study, a few application tests were developed internally to understand this issue. Two traditional liquid flux and two newly developed fluxes were selected to build up the basic models. The preliminary results also provide a scientific approach to design highly reliable products with the goal to minimize the reliability risk for the complex PCB designs and assembly processes.