20770-87-0

Basic information

• Product Name: methyl 3-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside
• Synonyms: methyl 3-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS NO: 20770-87-0
• Molecular Weight: 322.358
• Mol File: 20770-87-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 3-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside(20770-87-0)
• EPA Substance Registry System: methyl 3-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside(20770-87-0)

Safety Data

• Hazardous Substances Data: 20770-87-0(Hazardous Substances Data)

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 100662-74-6 methyl α-D-glucopyranoside 3-allyl ether 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 556-56-9 allyl iodid 
• 3162-96-7 (4aS,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 106-95-6 allyl bromide 
• 151937-60-9 methyl 2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucoside 
• 58341-56-3 Methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Relevant articles and documents

A Natural Lipotrisaccharide and Its Derivatives Selectively Lyse Streptococcus pneumoniae via Interaction with Cell Membrane

A natural lipotrisaccharide (NP000778, 1a), a new triglycosidic tri-O-substituted glycolipid isolated from the Morinda citrifolia plant, and its chemical derivatives were identified to be active against major Gram-positive pathogens, particularly Streptococcus pneumoniae. Additional evidence indicated that 1a and its synthetic derivatives exerted their bactericidal activities against S. pneumoniae by selectively targeting the bacterial membrane, leading to the rapid lysis of the pneumococci. Efficient synthesis of 1a and its derivatives was performed using an application of the intramolecular aglycon delivery (IAD) reaction to establish its structure-activity relationships (SARs). SAR analysis indicated that trisaccharide glycolipid compounds showed good selectivity and high potency against S. pneumoniae. These compounds contain a linear chain with a chain length from C3 to C9 at the 2-position (R1) and 4′-position (R3), as well as a 2-methyl butyryl group at the 3′-position (R2), without an aza substitution in the lipid chain. This is the first lipotrisaccharide identified with potent bactericidal activity via interaction with cell membrane. The results reported herein offer a valuable guideline for the design of glycolipid derivatives that selectively target pathogenic bacteria.

Synthesis, Photochemistry and Enzymology of 2-O-(2-Nitrobenzyl)-D-glucose, a Photolabile Derivative of D-Glucose

Alkylation of the dibutylstannylene derivative of methyl 4,6-O-benzylidene-α-D-glucopyranose 2a with 2-nitrobenzyl bromide gave a mixture of 2-O- and 3-O-(2-nitrobenzyl) derivatives 3b and 4 b in the ratio ca.3:1.Chromatographic separation and removal of the protecting groups gave the title compound 1.Regiospecific synthesis by 2-nitrobenzylation of the monoalcohol 8a was examined but could not be achieved efficiently.Compound 1 was neither a substrate for nor an inhibitor of coupled hexokinase/glucose-6-phosphate dehydrogenase enzyme system.On photolysis, it was converted into free glucose with 1:1 stoichiometry.

Regioselective alkylation of carbohydrates in metal complexes

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