74808-17-6

Basic information

• Product Name: methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• Synonyms: methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS NO: 74808-17-6
• Molecular Weight: 794.85
• Mol File: 74808-17-6.mol
• Article Data: 37

Chemical Properties

• CAS DataBase Reference: methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(74808-17-6)
• EPA Substance Registry System: methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(74808-17-6)

Safety Data

• Hazardous Substances Data: 74808-17-6(Hazardous Substances Data)

Upstream product

• 18311-26-7 methyl 6-O-triphenylmethyl-β-D-galactopyranoside 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 40653-30-3 methyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-galactopyranoside 
• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 1012045-70-3 methyl 2,3,4-tri-O-benzyl-6-O-(β-D-glucopyranosyl)-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 94575-69-6 2-iodophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 100432-86-8 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

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 articles and documents

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).

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.