A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of a Heptasaccharide Phytoalexin Elicitor (HPE)

1997 ◽  
Vol 119 (2) ◽  
pp. 449-450 ◽  
Author(s):  
K. C. Nicolaou ◽  
Nicolas Winssinger ◽  
Joaquín Pastor ◽  
Frederik DeRoose
Keyword(s):  
Total Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Highly Efficient

Facile Solid-Phase Synthesis of Sulfated Tyrosine-Containing Peptides: Total Synthesis of Human Big Gastrin-II and Cholecystokinin (CCK)-391,2

2001 ◽  
Vol 66 (1) ◽  
pp. 1-10 ◽  
Author(s):  
Kouki Kitagawa ◽  
Chikako Aida ◽  
Hidetoshi Fujiwara ◽  
Takeshi Yagami ◽  
Shiroh Futaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

scholarly journals Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

2013 ◽  
Vol 9 ◽  
pp. 2395-2403 ◽  
Author(s):  
Felix Wojcik ◽  
Sinaida Lel ◽  
Alexander G O’Brien ◽  
Peter H Seeberger ◽  
Laura Hartmann
Keyword(s):  
Double Bond ◽  
Building Block ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis ◽  
Highly Efficient ◽  
Monomer Sequence ◽  
Full Control ◽  
Block Approach

We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated solid-phase synthesis. Introduction of the sugar ligands via functionalized building blocks rather than postfunctionalization of the oligomeric backbone allows for the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.

scholarly journals The Pictet-Spengler Reaction Updates Its Habits

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 414 ◽  
Author(s):  
Andrea Calcaterra ◽  
Laura Mangiardi ◽  
Giuliano Delle Monache ◽  
Deborah Quaglio ◽  
Silvia Balducci ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Synthetic Method ◽  
Ring Closing Metathesis ◽  
Phase Synthesis ◽  
Acid Catalyzed ◽  
High Yields

The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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