161754-76-3

Upstream product

• 99-20-7 TREHALOSE 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-24-7 acetic anhydride 
• 18929-82-3 4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside 
• 80-10-4 diphenylsilyl dichloride 

Relevant academic research and scientific papers

Trehalose-based neuroprotective autophagy inducers

A small set of trehalose-centered putative autophagy inducers was rationally designed and synthesized, with the aim to identify more potent and bioavailable autophagy inducers than free trehalose, and to acquire information about their molecular mechanism

Synthesis of 4,6:2',3':4',6'-tri-O-cyclohexylidene-α,α'-trehalose 2-palmitate: An intermediate for the synthesis of mycobacterial 2,3-di-O-acyl-α,α'-trehalose antigens

The aim was to 'triprotect' trehalose by placing various acetals, or related protecting groups, across the 4,6-,2',3'-, and 4',6'-positions, leaving the 2,3-positions free for subsequent acylation. Isopropylidene and ethylidene acetals were studied, with the formation of a small amount of 4,6:2',3':4',6'tri-O-isopropylidene-α,α'-trehalose. 4,6:4',6'-Di-O-benzylidene-2',3'-O-(tetraphenyldisiloxane-1,3-diyl)-α ,α'-trehalose 2,3-diacetate was prepared in low yield. 1,1-Dimethoxycyclohexane reacted with methyl α-D-glucopyranoside to afford the 4,6-O-cyclohexylidene derivative, isolated as the diacetate; mild acid cleavage of the acetal gave the 2,3-diacetate. 4,6:2',3':4',6'-Tri-O-cyclohexylidene-α,α'-trehalose is the major product of the reaction between α,α'-trehalose and 1,1-dimethoxycyclohexane. 2,3:4,6:2',3':4',6'-Tetra-O-cyclohexylidene-, 4,6:4',6'-di-O-cyclohexylidene-, and 4,6-O-cyclohexylidene-α,α'-trehaloses were also isolated in lower yields, all acetals being characterised as their peracetates. The proportions of the different trehalose acetals were dependent upon the molar ratio of 1,1-dimethoxycyclohexane and particularly on the reaction temperature. The triprotected trehalose acetal was acylated with palmitic acid, with excellent regioselectivity, affording the 2-O-palmitoyl ester. This 2-monoacylated, triprotected trehalose is a key intermediate for the synthesis of 2,3-di-O-acyl-α,α'-trehalose glycolipid antigens, isolated from Mycobacterium fortuitum and Mycobacterium tuberculosis. The aim was to `triprotect' trehalose by placing various acetals, or related protecting groups, across the 4,6-, 2′,3′-, and 4′,6′-positions, leaving the 2,3-positions free for subsequent acylation. Isopropylidene and ethylidene acetals were studied, with the formation of a small amount of 4,6:2′, 3′:4′, 6′- tri-O- isopropylidene-α, α′-trehalose. 4,6:4′, 6′-Di-O-benzylidene-2′, 3′-O-(tetraphenyldisiloxane-1 ,3-d iyl)-α, α′-trehalose 2,3-diacetate was prepared in low yield. 1,1-Dimethoxycyclohexane reacted with methyl α-D-glucopyranoside to afford the 4,6-O-cyclohexylidene derivative, isolated as the diacetate; mild acid cleavage of the acetal gave the 2,3-diacetate. 4,6:2′,3′:4′,6′-Tri-O-cyclohexylidene- α,α′-t reha lose is the major product of the reaction between α,α′-trehalose and 1,1-dimethoxy-cyclohexane. 2,3:4,6:2′, 3′:4′, 6′-Tetra-O- cyclohexylidene-, 4,6:4′, 6′-di-O-cyclohexylidene-, and 4,6-O-cyclohexylidene-α,α′- trehaloses were also isolated in lower yields, all acetals being characterized as their peracetates. The proportions of the different trehalose acetals were dependent upon the molar ratio of 1,1-dimethoxycyclohexane and particularly on the reaction temperature. The triprotected trehalose acetal was acylated with palmitic acid, with excellent regioselectivity, affording the 2-O-palmitoyl ester. This monoacylated, triprotected trehalose is a key intermediate for the synthesis of 2, 3-di-O-acyl- α, α′-trehalose glycolipid antigens, isolated from Mycobacterium fortuitum and Mycobacterium tuberculosis.