Glycosylation from the non-reducing end using a combination of thioglycoside and glycosyl sulfoxide as the glycosyl donor and the acceptor.
TLDR
The present method would be useful for the block synthesis of glycosyl donors in the total synthesis of blanched oligosaccharides, especially when N-acetylglucosamines are presented at the non-reducing ends.Abstract:
A glycosylation reaction was performed using a combination of thioglycoside and glycosyl sulfoxide, which were prepared with odorless p-octyloxybenzenethiol, as a glycosyl donor and an acceptor, respectively. Promising results were obtained when p-octyloxylphenyl N-phthaloyl-D-thio-glucosaminide was activated with N-iodosuccinimide (NIS) and triflic acid (TfOH) for glycosylation of the hydroxyl group of the C-6 position of derivatives of D-glucosyl sulfoxide. Successive reduction of the resulting disaccharyl sulfoxides provided the corresponding thioglycosides, which could be used as the glycosyl donors in another glycosylation reaction to afford trisaccharides in good yield. The present method would be useful for the block synthesis of glycosyl donors in the total synthesis of blanched oligosaccharides, especially when N-acetylglucosamines are presented at the non-reducing ends.read more
Citations
More filters
Journal ArticleDOI
Glycosylation Reaction of Thioglycosides by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter.
TL;DR: The hypervalent iodine effectively induced glycosylation reaction of thioglycosides with various alcohols, featuring a high efficiency, completion in a short time, and proceeding under very mild conditions.
Journal ArticleDOI
Novel design and synthesis of a radioiodinated glycolipid analog as an acceptor substrate for N-acetylglucosaminyltransferase V.
Kenji Arimitsu,Kenji Arimitsu,Hiroyuki Kimura,Tetsuya Kajimoto,Tetsuya Kajimoto,Masahiro Ono,Yoshiro Ohmomo,Masayuki Yamashita,Manabu Node,Hideo Saji +9 more
TL;DR: A radiolabeled double-stranded glycolipid composed of a long-chain alkyl unit and a radioiodinated phenylalkyl unit is synthesized as a novel intravital glycolIPid mimic substrate of GnT-V.
Journal ArticleDOI
Alternative Synthesis of Radioiodinated Trisaccharide Derivatives, 2-(4-125Iodophenyl)ethyl 2-Acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranosyl-(1→6)-β-D-glucopyranoside, and Preparation of Its Analogs Having Different Lengths of Alkyl Chains Instead of Ethyl Group: Acceptor Substrates of N-Acetylglucosaminyltransferase V for in vivo Imaging
Masayuki Yamashita,Hideo Saji,Tetsuya Kajimoto,Hiroyuki Kimura,Masahiro Ono,Minoru Ozeki,Manabu Node,Yoshiro Ohmomo,Kenji Arimitsu +8 more
Journal ArticleDOI
Self-supported solution synthesis of oligosaccharides using thioglycosides donors / revision R2
TL;DR: In this paper , an alternative to the solution synthesis of oligosaccharides based on a polyol multiglycosylation was proposed, which was illustrated by the successful preparation of a tetraglucoside β (1−> 6) equipped with a propargylic linker, ready for conjugation by click chemistry.
References
More filters
Journal ArticleDOI
Glycosylation of unreactive substrates
TL;DR: Synthese de glucosteroide et d'arylglucoside a partir d'ethoxycarbonyloxy-3 hydroxy-7 cholanoate-24 acide et de phenyl tetra-O-benzyl-2,3,4,6 glucopyranosyl sulfoxyde
Journal ArticleDOI
A one-step synthesis of the ciclamycin trisaccharide
Subharekha Raghavan,Daniel Kahne +1 more
Journal ArticleDOI
Odorless substitutes for foul-smelling thiols: syntheses and applications
TL;DR: In this paper, the odors of alkanethiol and p-alkylphenylmethanethiols were compared by human and instrumental sensors, and it was revealed that these odorless thiols will greatly improve the physical environment of the researcher working with these foulsmelling compounds.
Journal ArticleDOI
Synthetic equivalents of benzenethiol and benzyl mercaptan having faint smell: odor reducing effect of trialkylsilyl group
TL;DR: This paper showed that trimethylsilyl substituent on the benzene ring has a remarkable effect in reducing the foul smell of the parent benzyl mercaptan and benzenethiol.
Journal ArticleDOI
New odorless method for the Corey-Kim and Swern oxidations utilizing dodecyl methyl sulfide (Dod-S-Me)
Shin-ichi Ohsugi,Kiyoharu Nishide,Keiji Oono,Kazunori Okuyama,Masato Fudesaka,Sumiaki Kodama,Manabu Node +6 more
TL;DR: In this article, Dod-S-Me was used as an alternative for dimethyl sulfide (DMS) and new odorless methods for the Corey-Kim and Swern oxidations were described.
Related Papers (5)
A New Method for α-Selective Glycosylation Using a Donor, Glycosyl Methyldiphenylphosphonium Iodide, without Any Assistance of Acid Promoters
Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors
Biao Yu,Houchao Tao +1 more
Highly α-Selective Glycosylation with Glycosyl Acetate via Glycosyl Phosphonium Iodide
Yohei Kobashi,Teruaki Mukaiyama +1 more