88988-46-9

Upstream product

• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 604-69-3 β-D-glucose pentaacetate 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 65827-55-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 29073-91-4 (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 3254-17-9 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 96323-23-8 benzyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 96323-23-8 benzyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 70255-93-5 Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 96323-30-7 methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 70255-93-5 Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 96323-29-4 methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 180714-32-3 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 207292-95-3 Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-tetrahydro-pyran-3-yl ester 
• 125085-08-7 methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 612499-94-2 allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 612499-89-5 allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside 
• 55659-53-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 851366-19-3 Acetic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trifluoro-N-phenyl-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

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.

Regio- and Stereoselective Synthesis of 1,2- cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis

Regio- and stereoselective synthesis of 1,2-cis-glycosides has been achieved by catalytic anomeric O-alkylation using organoboron compounds. Modulating steric and electronic factors of both catalysts and substrates enables activation of the axially oriented anomeric oxygens of glucose-derived dialkoxyborates. The mild reaction conditions allow broad functional-group tolerance. This approach can be applied to the efficient sequential synthesis of oligosaccharides.

Exploring glycosylation reactions under continuous-flow conditions

The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.

Total synthesis and absolute configuration of epicoccamide D, a naturally occurring mannosylated 3-acyltetramic acid

The endofungal metabolite epicoccamide D was synthesised in eighteen steps and 17 % yield as the first member of the family of natural glycotetramic acids. The modular character of the synthesis opens access also to analogues featuring different sugars and spacers. It comprises several high-yielding key steps. The β-D-mannosyl group was introduced by using an α-D-glucosyl imidate donor with subsequent oxidative-reductive epimerisation at C-2′. The pyrrolidine ring was closed quantitatively by a Lacey-Dieckmann condensation of an N-(β-ketoacyl)-N-methyl alaninate. The resulting 3-[ω-(β-D- mannosyl)octadec-2-enoyl]tetramic acid was hydrogenated in the presence of the rhodium catalyst (R,R)-[Rh(Et-DUPHOS)][BF4] to establish the (7S)-stereocentre. This was possible only after blocking the acyltetramic acid as a BF2-chelate to prevent capture of the metal catalyst. We also assigned the hitherto unknown configuration of the natural product as being 5S,7S by comparison of its 13C NMR spectroscopic and optical rotation data with those of our two synthetic 5S,7R/S-diasteromers. Copyright

Expedient and versatile formation of novel amino-deoxy-ketoheptuloses

Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-keto

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra

Benzyne arylation of oxathiane glycosyl donors

The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford a-glycosyl acetates in a 'one-pot' reaction, even in the presence of alternative acceptor alcohols.

Selective cleavage of sugar anomeric O-acyl groups using FeCl3·6H2O

A convenient method has been developed for regioselective anomeric deacylation of carbohydrate derivatives using FeCl3·6H2O in CH3CN. Operational simplicity, economic consideration, high yield, and low toxicity are key features associated with this protocol.

Synthesis of 3-O-(β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl)-3′-O-(β-d-glucopyranosyl)tamarixetin, the putative structure of aescuflavoside A from the seeds of Aesculus chinensis

3-O-(β-d-Xylopyranosyl-(1→2)-β-d-glucopyranosyl)-3′-O-(β-d-glucopyranosyl)tamarixetin, the putative flavonal glycoside named aescuflavoside A, isolated from the seeds of Aesculus chinensis, is synthesized via regioselective glycosylation of 7-O-benzyltama

Is acyl migration to the aglycon avoidable in 2-acyl assisted glycosylation reactions?

This report unequivocally separates orthoester formation from acyl transfer for the first time and indicates possible routes to eliminate 2-O-acyl transfer during glycosylation reactions. Experimental evidence is shown that acyl transfer from 2-O-acyl-3,4