149113-51-9

Upstream product

• 100-39-0 benzyl bromide 
• 18929-82-3 4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 99-20-7 TREHALOSE 

Downstream Products

• 41548-15-6 2,3,2',3'-tetra-O-benzyl-α,α-trehalose 
• 136090-72-7 2,3,6-Tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 125177-97-1 [(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol 
• 1456898-33-1 2,3,4,2',3'-penta-O-benzyl-4',6'-O-benzylidene-α,α-D-trehalose 
• 132183-33-6 2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzylidene-α-D-glucopyranoside 
• 132294-63-4 2',3'-di-O-benzyl-α-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1389320-87-9 C₅₂H₇₀O₁₁ 
• 956111-62-9 2,3,6-tri-O-benzyl-4-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,6-tri-O-benzyl-4-O-trifluoromethylsulfonyl-α-D-glucopyranoside 
• 441052-23-9 4-azido-4-deoxy-2,3,6-tri-O-benzyl-α-D-galactopyranosyl-[1->1]-4-azido-4-deoxy-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 441052-25-1 4,4'-diazido-4,4'-dideoxy-2,2',3,3',6,6'-hexa-O-benzyl-α-D-trehalose 
• 441052-30-8 4,4'-diamino-4,4'-dideoxy-2,2',3,3',6,6'-hexa-O-benzyl-α-D-trehalose 
• 441052-29-5 4-amino-4-deoxy-2,3,6-tri-O-benzyl-α-D-galactopyranosyl-[1->1]-4-amino-4-deoxy-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 441052-24-0 2,3,6-tri-O-benzyl-α-D-galactopyranosyl-[1->1]-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 441052-26-2 6,6'-di-O-acetyl-4,4'-diazido-4,4'-dideoxy-2,2',3,3'-tetra-O-benzyl-α-D-trehalose 

Relevant academic research and scientific papers

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.

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.

Synthesis and properties of dodecyl trehaloside detergents for membrane protein studies

Sugar-based detergents, mostly derived from maltose or glucose, prevail in the extraction, solubilization, stabilization, and crystallization of membrane proteins. Inspired by the broad use of trehalose for protecting biological macromolecules and lipid b

Convenient divergent synthesis of a library of trehalosamine analogues

(matrix presented) A library of seven trehalosamine analogues with various natural and non-natural binding motifs was synthesized through an expedient divergent synthetic approach. The final products were prepared in sufficient quantities and purities for

Water-soluble organometallic catalysts from carbohydrates. 1. Diphosphinite-Rh complexes

(matrix presented) Cyclohexylidene-protected diphosphinite-Rh complex A derived from α,α′-trehalose was treated with acidic resin in methanol to get the unprotected complex B, which is water soluble. Preparation of complexes A-C and their applications for hydrogenations show the problems and prospects of using water as a solvent for these reactions.