1352561-87-5

Basic information

• Product Name: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• Synonyms: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS NO: 1352561-87-5
• Molecular Weight: 923.026
• Mol File: 1352561-87-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(1352561-87-5)
• EPA Substance Registry System: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(1352561-87-5)

Safety Data

• Hazardous Substances Data: 1352561-87-5(Hazardous Substances Data)

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 72541-16-3 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose 
• 63783-77-7 2,3,4,6-tetra-O-acetyl-glucosylthioacetate 
• 190367-07-8 phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside 
• 1352561-50-2 C₃₀H₃₂O₇S 
• 323195-40-0 p-methylphenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

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.

Exploring and exploiting the reactivity of glucuronic acid donors

The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic acid esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiodisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.