74808-17-6

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 78687-40-8 methyl 2,3,4-tri-O-benzyl-6-O-(trimethylsilyl)-α-D-glucopyranoside 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 13350-45-3 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 830322-93-5 2,3,4,6-tetraacetylglucose-1-imidazolylcarbonyl 
• 838889-26-2 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-ethylcarbamoyloxy-tetrahydro-pyran-4-yl ester 
• 838889-22-8 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-chloro-acetylcarbamoyloxy)-tetrahydro-pyran-4-yl ester 
• 838889-20-6 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2-chloro-acetylcarbamoyloxy)-tetrahydro-pyran-4-yl ester 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 3019-71-4 Trichloroacetyl isocyanate 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 1012046-44-4 benzoxazolyl 2,3,4-tri-O-benzoyl-6-O-(3-hydroxycarbonylpropanoyl)-β-D-glucopyranoside 

Downstream Products

• 108671-41-6 (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

Phenyliodine bis(trifluoroacetate) (PIFA) as an excellent promoter of 2-deoxy-2-phthalimido-1-thioglycosides in the presence of triflic acid in glycosylation reactions

A combination of phenyliodine bis(trifluoroacetate) (PIFA) and trifluoromethanesulfonic acid was found to be an effective activator for the glycosylation reaction, of which the glycosyl donor was p-(octyloxy)phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido

β-Selective Glycosylation by Using O-Aryl-Protected Glycosyl Donors

New glycosyl donors have been developed that contained several para-substituted O-aryl protecting groups and their stereoselectivity for the glycosylation reaction was evaluated. A highly β-selective glycosylation reaction was achieved by using thioglycosides that were protected by 4-nitrophenyl (NP) groups, which were introduced by using the corresponding diaryliodonium triflate. Analysis of the stereoselectivities of several glycosyl donors indicated that the β-glycosides were obtained through an SN2-type displacement from the corresponding α-glycosyl triflate. The NP group could be removed by reduction of the nitro group and acylation, followed by oxidation with ceric ammonium nitrate (CAN).

MPTGs: Thioglycoside Donors for Acid-Catalyzed O-Glycosylation and Latent-Active Synthetic Strategies

4-(p-Methoxyphenyl)-4-pentenylthioglycosides (MPTGs) undergo acid-catalyzed O-glycosylation with a range of alcohol acceptors in the presence of 10 mol % of triflic acid at room temperature. Particularly encouraging is the reactivity of MPTGs toward unrea

Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

Two classes of thioglycoside, 4-(4-methoxyphenyl)-3-butenylthioglycosides (MBTGs) and 4-(4-methoxyphenyl)-4-pentenylthioglycosides (MPTGs), undergo acid-catalyzed O-glycosylations with a range of sugar and nonsugar alcohols at 25 °C. Electron density at t

O-acetylphenol ether glycosylation donor and preparation method and application thereof

The invention discloses an O-acetylphenol ether glycosylation donor, a preparation method thereof and application of the O-acetylphenol ether glycosylation donor in a glycosylation reaction. The O-acetylphenol ether glycosylation donor is stable, easy to store and widely used in various glycosylation reactions; the leaving group of the donor is the phenolic ether protecting group, and differing from operation of a benzyl ether protecting group, operation of phenolic ether protecting group can be conducted. The glycosylation reaction condition is mild, and all donors sensitive to acids and electrophilic reagents can accept the condition.

Removal of some common glycosylation by-products during reaction work-up

With the aim of improving the general glycosylation protocol to facilitate easy product isolation it was shown that amide by-products from glycosylation with trichloroacetimidate and N-phenyl trifluoroacetimidate donors could be removed during reaction work-up by washing with a basic aqueous solution. Excess glycosyl acceptor or lactol originating from glycosyl donor hydrolysis could equally be removed from the reaction mixture by derivatization with a basic tag and washing with an acidic solution during reaction work-up.

O-(p-Methoxyphenylethynyl)phenyl Glycosides: Versatile New Glycosylation Donors for the Highly Efficient Construction of Glycosidic Linkages

A novel alkyne-activation-based glycosylation protocol using o-(p-methoxyphenylethynyl)phenyl (MPEP) glycoside was established. The glycosyl MPEP donors were shelf-stable and could be prepared efficiently via Sonogashira reaction from the corresponding o-

AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature

Activation of sulfoxide as glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20–60 min), facile at room temperature and the reactions conditions tolerate acid sensitive groups.

A versatile glycosylation strategy: Via Au(III) catalyzed activation of thioglycoside donors

Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility w

Glycosylation with Disarmed Glycosyl Bromides Promoted by Iodonium Ions

Iodonium ions have been developed for activating glycosyl bromides in the coupling to glycosyl acceptors. The iodonium ions are generated from N-iodosuccinimide and a protic acid such as camphorsulfonic acid or triflic acid, where the latter gives the most reactive promoter system. The couplings occur with the release of iodine monobromide, and the best results are obtained with benzoylated glycosyl donors and acceptors. In this way, disarmed glycosyl bromides can serve as glycosyl donors without the use of heavy-metal salts.