71692-91-6

Upstream product

• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 128503-35-5 Pent-4-enyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 91298-42-9 methyl 2,3,6-tri-O-benzyl-4-O-trimethylsilyl-α-D-glucopyranoside 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 85618-27-5 n-dodecyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 179032-24-7 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-octadecylsulfanyl-tetrahydro-pyran-4-yl ester 
• 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 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 120593-63-7 3,4-epoxybutyl β-cellobioside 
• 1333164-03-6 methyl (sodium β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1333164-05-8 C₃₆H₄₁O₁₁^(1-)*Na⁽¹⁺⁾ 
• 1333164-04-7 methyl (sodium 2,3,4-tri-O-methyl-β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1333164-07-0 methyl (6-O-triphenylmethyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 88559-79-9 methyl (β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 88559-79-9 (2S,3R,4S,5R,6R)-2-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 108671-40-5 methyl 2,3,6-tri-O-benzyl-4-O-α-D-mannopyranosyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation

Challenges in the assembly of glycosidic bonds in oligosaccharides and glycoconjugates pose a bottleneck in enabling the remarkable promise of advances in the glycosciences. Here, we report a strategy that applies unique features of highly electrophilic b

METHODS FOR GLYCOSYLATION

Provided herein are methods of glycosylation in the formation of disaccharides, trisaccharides, and oligosaccharides using fluoroglycosides, silyl ether glycosides and a triaryl borane catalyst.

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

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

Glycosylation Enabled by Successive Rhodium(II) and Br?nsted Acid Catalysis

Herein, we reported on a highly efficient glycosylation reaction comprising two chronological meticulously designed catalytic cycles: (1) rhodium-catalyzed formation of sulfonium ylide and (2) Br?nsted acid-catalyzed formation of sulfonium ion. This protocol highlighted an effective and robust tactic to prepare a glycosyl sulfonium ion from a glycosyl sulfonium ylide precursor amenable for glycosylation.

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.

Iron(iii) chloride modulated selective 1,2-trans glycosylation based on glycosyl trichloroacetimidate donors and its application in orthogonal glycosylation

The development of a new glycosylation method for efficient stereoselective synthesis of β-gluco- and galactosides from their corresponding armed trichloroacetimidate donors mediated by 10 mole% of FeCl3 has been focused. FeCl3 has a

Remote Activation of Disarmed Thioglycosides in Latent-Active Glycosylation via Interrupted Pummerer Reaction

S-glycosides, S-2-(2-propylthio)benzyl (SPTB) glycosides, were converted to the corresponding oxidized glycosyl donors, S-2-(2-propylsulfinyl)benzyl (SPSB) glycosides, by simple and selective oxidation. Treatment of disarmed SPSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. Meanwhile, observation of thiosulfinate, thiosulfonate, and disulfide suggested that the leaving group was activated via an interrupted Pummerer reaction. The disarmed SPSB thioglycosyl donors could be selectively activated in the presence of various thioglycosides with remote activation mode. Finally, two natural hepatoprotective glycosides, Leonoside E and Leonuriside B, were efficiently synthesized in a convergent manner with this newly developed method.

AuCl3- and AuCl3-Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

Glycosylations of armed and disarmed trichloroacetimidate-based glycosyl donors were carried out by using the AuCl3-phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5-45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature. We have reported a convenient room temperature protocol that employs AuCl3 and phenylacetylene as a catalyst system to carry out the glycosylation of glycosyl trichloroacetimidates. The effectiveness of this relay catalyst system was also compared with that of using AuCl3 alone to catalyze the glycosylations.

2-Pyridyl glycoside: An alternative glycosyl donor in preactivation protocol

2-Pyridyl glycosides have been identified to be powerful glycosyl donors for the preactivation-based oligosaccharide synthesis. By using stoichiometric amount of Tf2O, the 2-pyridyl glycosides were pre-activated, which subsequently underwent gl