18929-82-3

Basic information

• Product Name: 4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside
• Synonyms: 4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside
• CAS NO: 18929-82-3
• Molecular Weight: 518.518
• Mol File: 18929-82-3.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: 4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside(18929-82-3)
• EPA Substance Registry System: 4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside(18929-82-3)

Safety Data

• Hazardous Substances Data: 18929-82-3(Hazardous Substances Data)

Upstream product

• 99-20-7 TREHALOSE 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 32849-07-3 4,6:4',6'-di-O-benzylidene-α,α-trehalose 2,2'-ditosylate 
• 585-91-1 neotrehalose 

Downstream Products

• 147347-39-5 4,6:4',6'-di-O-benzylidene-2-O-stearoyl-α,α-trehalose 
• 577969-86-9 2,3,2',3'-tetra-O-benzoyl-4,6:4',6'-di-O-benzylidene-α,α-trehalose 
• 18968-33-7 Methanesulfonic acid (4aR,6R,7R,8S,8aR)-6-((4aR,6R,7R,8S,8aR)-7,8-bis-methanesulfonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-7-methanesulfonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 75712-61-7 4,6;4',6'-di-O-benzylidene-2-O-palmitoyl-α,α'-trehalose 
• 32849-13-1 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranosyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 32849-09-5 4,6:4'6'-di-O-benzylidene-α,α-trehalose 2-tosylate 
• 32849-07-3 4,6:4',6'-di-O-benzylidene-α,α-trehalose 2,2'-ditosylate 
• 32849-10-8 4,6:4,'6'-di-O-benzylidene-α,α-trehalose 2,3,2'-tritosylate 
• 33072-96-7 4,6:4,'6'-di-O-benzylidene-α,α-trehalose 2,3,2',3'-tetratosylate 
• 75712-63-9 4,6;4',6'-di-O-benzylidene-2,2'-di-O-palmitoyl-α,α'-trehalose 
• 75721-17-4 4,6;4',6'-di-O-benzylidene-2,2',3-tri-O-palmitoyl-α,α'-trehalose 
• 82305-37-1 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 129727-78-2 4,6-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranosyl 4,6-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside 
• 91667-48-0 ammonium 4,6:4',6'-di-O-benzylidene-α,α-trehalose 2-sulfate 

Relevant articles and documents

Synthesis, trehalase hydrolytic resistance and inhibition properties of 4- and 6-substituted trehalose derivatives

Although trehalose has recently gained interest because of its pharmaceutical potential, its clinical use is hampered due to its low bioavailability. Hence, hydrolysis-resistant trehalose analogues retaining biological activity could be of interest. In this study, 34 4- and 6-O-substituted trehalose derivatives were synthesised using an ether- or carbamate-type linkage. Their hydrolysis susceptibility and inhibitory properties were determined against two trehalases, i.e. porcine kidney and Mycobacterium smegmatis. With the exception of three weakly hydrolysable 6-O-alkyl derivatives, the compounds generally showed to be completely resistant. Moreover, a number of derivatives was shown to be an inhibitor of one or both of these trehalases. For the strongest inhibitors of porcine kidney trehalase IC50 values of around 10 mM could be determined, whereas several compounds displayed sub-mM IC50 against M. smegmatis trehalase. Dockings studies were performed to explain the observed influence of the substitution pattern on the inhibitory activity towards porcine kidney trehalase.

Trehalose-cored amphiphiles for membrane protein stabilization: Importance of the detergent micelle size in GPCR stability

Despite their importance in biology and medicinal chemistry, structural and functional studies of membrane proteins present major challenges. To study diverse membrane proteins, it is crucial to have the correct detergent to efficiently extract and stabilize the proteins from the native membranes for biochemical/biophysical downstream analyses. But many membrane proteins, particularly eukaryotic ones, are recalcitrant to stabilization and/or crystallization with currently available detergents and thus there are major efforts to develop novel detergents with enhanced properties. Here, a novel class of trehalose-cored amphiphiles are introduced, with multiple alkyl chains and carbohydrates projecting from the trehalose core unit are introduced. A few members displayed enhanced protein stabilization behavior compared to the benchmark conventional detergent, n-dodecyl-β-d-maltoside (DDM), for multiple tested membrane proteins: (i) a bacterial leucine transporter (LeuT), (ii) the R. capsulatus photosynthetic superassembly, and (iii) the human β2 adrenergic receptor (β2AR). Due to synthetic convenience and their favourable behaviors for a range of membrane proteins, these agents have potential for membrane protein research. In addition, the detergent property-efficacy relationship discussed here will guide future design of novel detergents.

Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals

Trehalose dibenzylidene and substituted dibenzylidene acetals were reductively opened either at O6 or O4 in a regioselective manner by using a DIBAL stock solution prepared in toluene or dichloromethane, respectively, to achieve desymmetrization of the trehalose core. The method was applied to synthesize various biologically important unsymmetrically substituted trehalose glycoconjugates, including a mycobacterial trisaccharide, a 4-epi-trehalosamine analog and a maradolipid.