1621188-46-2

Basic information

• Product Name: methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside
• Synonyms: methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside
• CAS NO: 1621188-46-2
• Molecular Weight: 943.335
• Mol File: 1621188-46-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside(1621188-46-2)
• EPA Substance Registry System: methyl 2,3,6-tri-O-benzyl-4-O-(2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside(1621188-46-2)

Safety Data

• Hazardous Substances Data: 1621188-46-2(Hazardous Substances Data)

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1621188-31-5 6-O-benzyl-1,2-dideoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-arabino-1-hexenopyranose 
• 165524-85-6 6-O-(benzyl)-D-glucal 
• 100-39-0 benzyl bromide 
• 13265-84-4 D-glucal 

Relevant articles and documents

Cooperative Br?nsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides

A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Br?nsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.

Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.