Pyranoside-into-Furanoside Rearrangement of 4-Pentenyl Glycosides in the Synthesis of a Tetrasaccharide-Related to Galactan I ofKlebsiella pneumoniae

2017 ◽  
Vol 2017 (3) ◽  
pp. 710-718 ◽  
Author(s):  
Stella A. Verkhnyatskaya ◽  
Vadim B. Krylov ◽  
Nikolay E. Nifantiev
Keyword(s):  
Pentenyl Glycosides

Glycosyl fluorides from n-pentenyl-related glycosyl donors — Application to glycosylation strategies

2013 ◽  
Vol 91 (1) ◽  
pp. 51-65 ◽  
Author(s):  
Bert Fraser-Reid ◽  
J. Cristobal Lopez ◽  
Paloma Bernal-Albert ◽  
Ana M. Gomez ◽  
Clara Uriel ◽  
...  
Keyword(s):  
Pyridine Complex ◽  
Pentenyl Glycosides ◽  
Glycosyl Donors

n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga’s reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy2BF4), gives good yields of glycosyl fluorides when HF–pyridine complex is used as an additional fluoride source. NPOEs can be activated either by a combination of electrophilic iodonium (Barluenga’s reagent) and HBF4 or by the action of HF–pyridine complex. The ensuing glycosyl fluorides form a semiorthogonal pair of glycosyl donors when confronted with NPGs.

IPy2BF4-Mediated Transformation ofn-Pentenyl Glycosides to Glycosyl Fluorides:  A New Pair of Semiorthogonal Glycosyl Donors

2007 ◽  
Vol 9 (15) ◽  
pp. 2759-2762 ◽  
Author(s):  
J. Cristóbal López ◽  
Clara Uriel ◽  
Alejandra Guillamón-Martín ◽  
Serafín Valverde ◽  
Ana M. Gómez
Keyword(s):  
Pentenyl Glycosides ◽  
Glycosyl Donors

Comparing n-pentenyl orthoesters and n-pentenyl glycosides as alternative glycosyl donors

Tetrahedron ◽  
2002 ◽  
Vol 58 (36) ◽  
pp. 7345-7354 ◽  
Author(s):  
Mateusz Mach ◽  
Urs Schlueter ◽  
Felix Mathew ◽  
Bert Fraser-Reid ◽  
Kevin C Hazen
Keyword(s):  
Pentenyl Glycosides ◽  
Glycosyl Donors

ChemInform Abstract: The Chemistry of N-Pentenyl Glycosides: Synthetic, Theoretical, and Mechanistic Ramifications

ChemInform ◽  
2010 ◽  
Vol 24 (26) ◽  
pp. no-no
Author(s):  
B. FRASER-REID ◽  
J. R. MERRITT ◽  
A. L. HANDLON ◽  
C. W. ANDREWS
Keyword(s):  
Pentenyl Glycosides

n-Pentenyl Glycosides in Organic Chemistry: A Contemporary Example of Serendipity

Synlett ◽  
1992 ◽  
Vol 1992 (12) ◽  
pp. 927-942 ◽  
Author(s):  
Bert Fraser-Reid ◽  
Uko E. Udodong ◽  
Zufan Wu ◽  
Hakan Ottosson ◽  
J. Robert Merritt ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Pentenyl Glycosides

ChemInform Abstract: Glycosylation Methods: Use of N-Pentenyl Glycosides

ChemInform ◽  
2001 ◽  
Vol 32 (12) ◽  
pp. no-no
Author(s):  
Bert Fraser-Reid ◽  
G. Anilkumar ◽  
Mark R. Gilbert ◽  
Subodh Joshi ◽  
Ralf Kraehmer
Keyword(s):  
Pentenyl Glycosides

A Fluorinated Selenide Linker for Solid-Phase Synthesis ofn-Pentenyl Glycosides

2004 ◽  
Vol 6 (26) ◽  
pp. 4885-4888 ◽  
Author(s):  
Mickael Mogemark ◽  
Linda Gustafsson ◽  
Christoffer Bengtsson ◽  
Mikael Elofsson ◽  
Jan Kihlberg
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Pentenyl Glycosides

ChemInform Abstract: Use of n-Pentenyl Glycosides as Precursors to Various Spacer Functionalities.

ChemInform ◽  
2010 ◽  
Vol 31 (22) ◽  
pp. no-no
Author(s):  
Therese Buskas ◽  
Eva Soederberg ◽  
Peter Konradsson ◽  
Bert Fraser-Reid
Keyword(s):  
Pentenyl Glycosides

Orthogonal Activation of Propargyl andn-Pentenyl Glycosides and 1,2-Orthoesters

2009 ◽  
Vol 74 (23) ◽  
pp. 9233-9236 ◽  
Author(s):  
Srinivasa Rao Vidadala ◽  
Shivaji A. Thadke ◽  
Srinivas Hotha
Keyword(s):  
Pentenyl Glycosides
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