76054-83-6

Basic information

• Product Name: 6-O-trityl-α,α-trehalose
• Synonyms: 6-O-trityl-α,α-trehalose
• CAS NO: 76054-83-6
• Molecular Weight: 584.62
• Mol File: 76054-83-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 6-O-trityl-α,α-trehalose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-trityl-α,α-trehalose(76054-83-6)
• EPA Substance Registry System: 6-O-trityl-α,α-trehalose(76054-83-6)

Safety Data

• Hazardous Substances Data: 76054-83-6(Hazardous Substances Data)

Upstream product

• 99-20-7 TREHALOSE 
• 76-83-5 trityl chloride 
• 113842-78-7 6-trityl-2,3,4,2’,3’,4’6’-hepta-O-acetyl-α,α’-D-trehalose 

Downstream Products

• 113842-78-7 6-trityl-2,3,4,2’,3’,4’6’-hepta-O-acetyl-α,α’-D-trehalose 

Relevant articles and documents

Rational design of first generation inhibitors for trehalose 6-phosphate phosphatases

In this study, trehalose 6-phosphate phosphatase (T6PP) was targeted for inhibitor development. T6PP catalyzes the hydrolysis of trehalose-6-phosphate to form trehalose and inorganic phosphate, a reaction essential to important fungal, bacterial, and nematodal pathogens. At the current time, there are no specific inhibitors of T6PP available to serve as tools for interrogating its structure and function nor as leads for pharmaceutical applications. Herein, we describe the synthesis of non-hydrolysable mimics of trehalose-6-phosphate, which incorporate 6-sulfate (1), -phosphonate (2), -fluorophosphonate (3) and –boronate (4) groups in place of the 6-phosphate moiety of the substrate. The inhibitory efficacies of these adducts were evaluated against trehalose 6-phosphate phosphatases selected from evolutionarily distant pathogenic bacteria and nematodes. Phosphonates 2 and 3 were found to display good inhibitory activities against the T6PPs, while the sulfate analog, trehalose-6-sulfate, proved to be a particularly effective broad-spectrum inhibitor of these phosphatases and an ideal prototype for optimization.

Synthetic Studies toward Pyruvate Acetal Containing Saccharides. Synthesis of the Carbohydrate Part of the Mycobacterium smegmatis Pentasaccharide Glycolipid and Fragments Thereof for the Preparation of Neoantigens

A series of 2,3-di-O-benzoyl-4,6-O--D-glucopyranosyl donors (β-phenylthio 3, bromide 4, α-chloride 5, β-fluoride 6, and trichloroacetimidate 7) were prepared from the corresponding α-allyl glucoside 1 via the deallylated glucose 2 and were tested in glycosylation reactions with methanol to give the pyruvylated methyl glucosides 8 and 9 and with methyl 2,4,6-tri-O-benzoyl-β-D-glucopyranoside 10 to give the disaccharide 11.Best result with respect to yield and β-selectivity of the coupling were achieved with imidate 7.Thus, the 2-O-benzoyl-4,6-O--3-O-methyl-D-glucopyranosyl trichloroacetimidate 14 was prepared from its benzyl glucoside 12 and used for the synthesis of fragments related to the Mycobacterium smegmatis lipopentasaccharide.Trimethylsilyl trifluoromethanesulfonate-mediated condensation of 14, 5-pentanol, and 10, respectively, followed by deblocking of the products 15 and 17 gave the pyruvylated aminopentyl glucoside 16 and methyl laminaribioside 18.Treatment of 17 with dichloromethyl methyl ether gave the laminaribiosyl chloride 19, coupling of which with protected 5-aminopentanol gave 20 also obtained from 14 and the monosaccharide nucleophile 26.The trisaccharide 5-aminopentyl glycoside fragment 42 was prepared by first coupling of 14 and benzyl 2-O-benzoyl-4,6-O--α-D-glucopyranoside 30 that was converted to the bispyruvylated laminaribiose imidate 33, followed by condensation with thioglycoside 38 obtainable in four steps from 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose to give the trisaccharide ethyl thioglycoside 40.Next, NIS-mediated condensation of 40 and 5-pentanol followed by deblocking gave 42.Pentasaccharide 45 was similarly prepared from 40 and hepta-O-benzoyltrehalose 43 to give first the blocked saccharide 44, deblocking of which afforded the target pentasaccharide.