38992-91-5

Upstream product

• 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 
• 64-19-7 acetic acid 
• 149113-51-9 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 
• 100-39-0 benzyl bromide 
• 99-20-7 TREHALOSE 
• 128242-05-7 C₅₄H₅₄O₁₁ 
• 18929-82-3 C₂₆H₃₀O₁₁ 
• 585-91-1 neotrehalose 

Downstream Products

• 39021-77-7 2,3,2',3'-tetra-O-benzyl-6,6'-di-O-p-tolylsulfonyl-α,α-trehalose 
• 107909-01-3 2,3,2',3'-tetra-O-benzyl-6-O-p-tolylsulfonyl-α,α-trehalose 
• 82305-39-3 2,3,2',3'-tetra-O-benzyl-6-O-stearoyl-α,α-trehalose 
• 82305-38-2 2,3,2',3'-tetra-O-benzyl-6,6'-di-O-stearoyl-α,α-trehalose 
• 1389320-87-9 C₅₂H₇₀O₁₁ 
• 1389320-88-0 C₅₂H₇₀O₁₁ 
• 39021-77-7 2,3,2',3'-tetra-O-benzyl-6,6'-di-O-p-tolylsulfonyl-α,β-trehalose 
• 107909-02-4 2,3,2',3'-tetra-O-benzyl-6-O-corynomycoloyl-α,α-trehalose 
• 68681-65-2 6-O-corynomycoloyl-α,α-trehalose 
• 81105-71-7 2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-p-tolylsulfonyl-α,α-trehalose 
• 149018-92-8 methyl <(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-heptopyranosyluronate) 2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-heptopyranosid>uronate 
• 149018-93-9 (2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-heptopyranosyluronic acid) 2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-heptopyranosiduronic acid 
• 441052-21-7 2,3-di-O-benzyl-6-deoxy-α-D-galactopyranosyl-[1->1]-2,3-di-O-benzyl-6-deoxy-α-D-galactopyranoside 
• 216572-25-7 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranosyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

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

Synthesis of mirror coryno cord factors

A protected bis-heptosiduronic acid, (2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-heptopyranosyluronic acid) 2,3,4-tri-O-benzyl-6-deoxy-α-D-gluco-heptopyranosiduronic acid, was synthesized by the iron carbonyl method of chain elongation, starting from 2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-tosyl-α,α-trehalose.Its dimethyl ester was also prepared by acid-catalyzed methanolysis of its diamide, previously obtained by another route.Mitsunobu esterification of the diacid with (racemic) (2RS,3SR)- and (2RS,3RS)-3-O-benzylcorynomycolyl alcohols, obtained by reduction of synthetic, 3-O-benzylated methyl C32-corynomycolates with lithium aluminum hydride, furnished the corresponding diesters in high yields.Hydrogenolytic debenzylation of the products led to "mirror" coryno cord factors.

Chemical synthesis and biological activities of 6,6'-di-O-mycoloyl-beta,beta- and -alpha,beta-trehalose.

6,6'Di-O-mycoloyl-beta,beta-trehalose (beta,beta-TDM) and 6,6'-di-O-mycoloyl-alpha,beta-trehalose (alpha,beta-TDM) were synthesized and their toxicity and ability to activate peritoneal macrophages in situ were examined in mice, in comparison with 6,6'-di

α-D-Glycosyl-Substituted α,α-D-Trehaloses with (1 -> 4)-Linkage: Syntheses and NMR Investigations

Two symmetrical trehalose glycosyl 'acceptors' 4 and 6 were prepared and three of the unsymmetrical type, 8, 10, and 11.Glucosylation of symmetrical 'acceptor'4 gave a higher yield of trisaccharide (44percent) than protective-group manipulation, namely vi

Chemical and Biochemical Studies on Carbohydrate Esters. XIII. Synthesis of 6-O-, 6,6'-Di-O-, and 4,6,4',6'-Tetra-O-stearoyl-α,α-trehaloses

2,3,2',3'-Tetra-O-benzyl-α,α-trehalose was synthesized conveniently in improved yield according to the know pathway but under modified reaction conditions: namely, α,α-trehalose was treated with α,α-dimethoxytoluene to give its 4,6:4',6'-di-O-benzylidene derivative, which was benzylated with benzyl chloride in dimethylsulfoxyde in the presence of sodium hydride, and subsequently debenzylidenated by hydrolysis with 80percent acetic acid.Selective acylation of the key intermediate by reaction with 1.4 molar equivalents of stearoyl chloride, followed by catalytic hydrogenolysis over palladium black, afforded 6-O-stearoyl-α,α-trehalose, mp 116-122 deg C, +108.2 deg (c=1.0, chloroform), and 6,6'-di-O-stearoyl-α,α-trehalose, mp 157-160 deg C, +80.8 deg (c=1.0, chloroform), in an approximate molar ratio of 1:3.8.Similarly, 4,6,4',6'-tetra -O-stearoyl-αα-trehalose, mp 95-97 deg C and 108-110 deg C (double melting point), +54.5 deg (c=1.0, chloroform), was also obtained by the use of 4 molar equivalents of acid chloride.Based on comparison of the carbon-13 nuclear magnetic resonance ((13)C NMR) spectral data and thin-layer and gas-liquid chromatographic behavior, the major components contained in the mono- and diester preparations which had been produced in our previous work by transesterification of α,α-trehalose with methyl stearate and shown to possess interesting biological activities were identified as the 6- and 6,6'-stearates, respectively.Keywords---synthesis; 6-O-stearoyl-α,α-trehalose; 6.6'-di-O-stearoyl-α,α-trehalose; 4,6,4',6',-tetra-O-stearoyl-α,α-trehalose; 4,6:4',6'-di-O-benzylidene-α,α-trehalose; 2,3,2',3'-tetra-O-benzyl-α,α-trehalose; (13)C NMR