79218-68-1

Basic information

• Product Name: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• Synonyms: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS NO: 79218-68-1
• Molecular Weight: 492.569
• Mol File: 79218-68-1.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside(79218-68-1)
• EPA Substance Registry System: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside(79218-68-1)

Safety Data

• Hazardous Substances Data: 79218-68-1(Hazardous Substances Data)

Upstream product

• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 64-19-7 acetic acid 
• 3254-17-9 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranoside 
• 68681-00-5 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 
• 80065-87-8 1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 28140-37-6 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 83-87-4 D-Mannose pentaacetate 
• 108-24-7 acetic anhydride 
• 80877-03-8 3,4,6-tri-O-acetyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 
• 68567-54-4 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 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 
• 96323-28-3 methyl-2,3,4-tri-O-benzyl-6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 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 
• 125897-95-2 C₆₀H₇₈O₁₀ 
• 125897-95-2 C₆₀H₇₈O₁₀ 
• 152871-96-0 phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 343565-50-4 2-acetyl-3,4,6-tri-O-benzylglucopyranose-N-tosylcarbamate 
• 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 
• 108869-65-4 5-Methyl-2-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)furan 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

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.

Targeted delivery of fluorescent high-mannose-type oligosaccharide cathepsin inhibitor conjugates

Abstract Three fluorescent cathepsin inhibitor glycoconjugates have been designed, synthesized, and evaluated in terms of their cell internalization and cathepsin inhibitory properties. The conjugates are composed of a peptide epoxysuccinate, capable of c

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.