3-(Tributylstannyl)allyl Alcohols: Useful Building Blocks for Solid-Phase Synthesis of Skipped Dienes and Trienes

2000 ◽  
Vol 65 (3) ◽  
pp. 434-454 ◽  
Author(s):  
Miroslav Havránek ◽  
Dalimil Dvořák
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Solid Support ◽  
Stille Coupling ◽  
Phase Synthesis ◽  
Negative Results ◽  
Allyl Alcohols

Repeated Stille coupling of 3-substituted 3-(tributylstannyl)allyl alcohols 2 on a solid support was used to synthesize a 21 × 21 library of skipped dienes and a 21 × 21 × 21 library of skipped trienes. Starting 3-(tributylstannyl)allyl alcohols were prepared by Pd-catalyzed hydrostannation of substituted prop-2-yn-1-ols, by hydroalumination by LiAlH4 followed with transmetallation to tin using tributyltin methoxide, or by substitution of chlorine in (Z)-6-chloro-3-(tributylstannyl)hex-2-en-1-ol with appropriate nucleophile. Synthesized libraries were tested for the activity to endorphin receptors, but with negative results.

scholarly journals The Breaking Beads Approach for Photocleavage from Solid Support

2020 ◽  
Author(s):  
yasmeen bakhatan ◽  
Israel Alshanski ◽  
Dana Grunhaus ◽  
Mattan Hurevich
Keyword(s):  
Continuous Flow ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
High Energy ◽  
Solid Support ◽  
Phase Synthesis ◽  
Polystyrene Beads ◽  
Magnetic Stirring ◽  
Photolabile Linkers

Photocleavage from polystyrene beads is a pivotal reaction for solid phase synthesis that relies on photolabile linkers. The photocleavage, usually performed by batch irradiation, suffers from incomplete and slow cleavage. To overcome these issues, continuous flow and high-energy lamps are frequently used, but these setups are hazardous, technically challenging, and expensive. We developed a photocleavage approach that relies on a benchtop LED lamp and magnetic stirring. In this approach, we crush the beads instead of keeping their integrity to increase the yield of photocleavage. This approach proved very efficient for photocleavage of protected oligosaccharides.

scholarly journals Recovery, Purification, and Reusability of Building Blocks for Solid Phase Synthesis

2019 ◽  
Vol 41 (2) ◽  
pp. 1900473
Author(s):  
Fadi Shamout ◽  
Lukas Fischer ◽  
Nicole L. Snyder ◽  
Laura Hartmann
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis

A New Linker for Solid-Phase Synthesis of Oligonucleotides with Terminal Phosphate Group

2008 ◽  
Vol 73 (1) ◽  
pp. 32-43 ◽  
Author(s):  
Ondřej Pačes ◽  
Zdeněk Točík ◽  
Ivan Rosenberg
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
Phosphate Group ◽  
Phase Synthesis ◽  
Terminal Phosphate Group

Synthesis of a novel cyanoethyl-type linker suitable for the solid-phase synthesis of oligodeoxynucleotides possessing terminal 3'-phosphate group is described. Since the linker is a 2-substituted 2-cyanoethanol, the release of the synthesized oligonucleotide from the solid support is accomplished by β-elimination in the ammonia deprotection step.

Concise solid-phase synthesis of inverse poly(amidoamine) dendrons using AB2 building blocks

2013 ◽  
Vol 49 (51) ◽  
pp. 5784 ◽  
Author(s):  
Adela Ya-Ting Huang ◽  
Ching-Hua Tsai ◽  
Hsing-Yin Chen ◽  
Hui-Ting Chen ◽  
Chi-Yu Lu ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis

scholarly journals Modular automated solid phase synthesis of dermatan sulfate oligosaccharides

2014 ◽  
Vol 50 (15) ◽  
pp. 1875-1877 ◽  
Author(s):  
Jeyakumar Kandasamy ◽  
Frank Schuhmacher ◽  
Heung Sik Hahm ◽  
James C. Klein ◽  
Peter H. Seeberger
Keyword(s):  
Solid Phase Synthesis ◽  
Dermatan Sulfate ◽  
Solid Phase ◽  
Building Blocks ◽  
Automated Synthesis ◽  
Phase Synthesis ◽  
Iduronic Acid

Orthogonally protected d-galactosamine and l-iduronic acid building blocks and a photo-cleavable linker are instrumental for the automated synthesis of dermatan sulfate oligosaccharides.

Sign in / Sign up

Export Citation Format

Share Document