ChemInform Abstract: Protecting Groups in Oligosaccharide Synthesis

ChemInform ◽  
2010 ◽  
Vol 28 (36) ◽  
pp. no-no
Author(s):  
T. B. GRINDLEY
ChemInform ◽  
2007 ◽  
Vol 38 (10) ◽  
Author(s):  
Takeshi Yamada ◽  
Kazunobu Takemura ◽  
Jun-ichi Yoshida ◽  
Shigeru Yamago

2007 ◽  
Vol 342 (3-4) ◽  
pp. 419-429 ◽  
Author(s):  
Remy E.J.N. Litjens ◽  
Leendert J. van den Bos ◽  
Jeroen D.C. Codée ◽  
Herman S. Overkleeft ◽  
Gijsbert A. van der Marel

2022 ◽  
pp. 39-46
Author(s):  
Ntai M Khoabane ◽  
Elizabeth J Grayson ◽  
Alan M Kenwright ◽  
Manoharan K Pillai

Oligosaccharides have been playing an important role in biological systems. Synthesis of oligosaccharides requires the protection from hydroxyl groups present in the corresponding monosaccharide units. The existing methods of protection have drawbacks, including formation of anomeric mixtures, change in hydrophilicity or lipophilicity and solubility of the products, participation of the protecting groups in the reactions of the core of monosaccharide units, problems associated with chemoselectivity, regioselectivity and overall stereochemical outcomes of reactions. Additionally, there has been a spectral overlap of these protecting groups with carbohydrate core, which yielded more complex spectra. Therefore, the identification and synthesis of suitable alternative protecting groups have received attention in the oligosaccharide synthesis. The objective of the present study was to synthesize various fluorinated benzyl ethers of methyl-α-D-mannopyronoside and to evaluate these ethers as the alternative protecting groups for enhancing NMR resolution in the oligosaccharide synthesis. Various fluorinated benzyl ethers of methyl-α-D-mannopyronoside were prepared through the reaction of methyl-α-D-mannopyronoside with various fluorinated benzyl bromides by using Williamson ether synthesis method. Spectral analysis of these fluorinated benzyl ethers showed that the peaks of methylene carbons shifted to a value of 10-20 parts per million (ppm) to a high field region in the 13C NMR, compared to the non-fluorinated benzyl ether. As a result, the spectral complexity decreased and enhanced the spectral resolution. In this study, we concluded that fluorinated benzyl ethers could be a suitable alternative to the non-fluorinated benzyl ethers to protect the hydroxyl groups of monosaccharides in the synthesis of oligosaccharides.


Synlett ◽  
1998 ◽  
Vol 1998 (5) ◽  
pp. 487-488 ◽  
Author(s):  
G. G. Cross ◽  
D. M. Whitfield

2006 ◽  
Vol 118 (45) ◽  
pp. 7737-7740 ◽  
Author(s):  
Takeshi Yamada ◽  
Kazunobu Takemura ◽  
Jun-ichi Yoshida ◽  
Shigeru Yamago

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 880-884
Author(s):  
Mattan Hurevich ◽  
Mamidi Samarasimhareddy ◽  
Israel Alshanski ◽  
Evgeniy Mervinetsky

Permanent protecting groups are essential for oligosaccharide synthesis. However, the removal of the traditionally used protecting groups is not trivial and demands considerable expertise. Using photolabile protecting groups as permanent protection for glycan can overcome many limitations associated with the traditional oligosaccharide synthesis approach. It is demonstrated here that up to eight photolabile protecting groups can be readily removed from a single glycan using a benchtop LED setup that is very easy to operate. This report suggests that further development of the strategy will offer an attractive alternative for oligosaccharide synthesis.


Sign in / Sign up

Export Citation Format

Share Document