76951-66-1

Upstream product

• 76-83-5 trityl chloride 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 341-02-6 trityl tetrafluoroborate 
• 85326-15-4 3,4-di-O-acetyl-1,2-O-<1-(endo-cyano)ethylidene>-α-D-xylopyranose 
• 312493-51-9 (((4-methoxybenzyl)oxy)methanetriyl)tribenzene 
• 76-84-6 triphenylmethyl alcohol 
• 141561-63-9 (((3-methylbut-2-en-1-yl)oxy)methanetrityl)tribenzene 

Downstream Products

• 80763-58-2 1,3,4,6-tetra O-benzoyl-α-fructofuranosyl-(2->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 26184-96-3 rutinose 
• 62043-20-3 1,2:3,4-di-O-isopropylidene-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-galactopyranose 
• 5239-08-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-O-diisopropylidene-α-D-galactopyranose 
• 86782-41-4 p-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranoside 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 3646-73-9 α-D-galactopyranose 
• 60945-40-6 O¹,O²-isopropylidene-α-D-galactopyranose 
• 552-74-9 6-O-α-L-rhamnopyranosyl-D-galactose 

Relevant academic research and scientific papers

Novel selectivity in carbohydrate reactions, IV: DABCO-mediated regioselective primary hydroxyl protection of carbohydrates

An efficient procedure for the regioselective tritylation of primary hydroxyl group of aldohexopyranosides and nucleosides using trityl chloride in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in dichloromethane has been developed. Subsequent acetylation of the tritylated products in the same pot has been made possible, thereby providing an efficient route to the fully protected carbohydrate derivatives that can be discriminated chemoselectively.

Application of ball milling technology to carbohydrate reactions: I. Regioselective primary hydroxyl protection of hexosides and nucleoside by planetary ball milling

Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.

Alternative reagents for the tritylation of alcohols

Two new tritylation reagents [viz. p-methoxybenzyl trityl ether (p-MBTE) and prenyl trityl ether (PTE)] were prepared. These two new reagents were utilized efficiently for the tritylation of alcohols, using DDQ or 20 mol% DDQ-3 eq. Mn(OAc)3. Copyright Tay

Mild benzhydrylation and tritylation of saccharidic hydroxyls promoted by acid washed molecular sieves

Commercially available 4 ? acid washed molecular sieves (AW 300 MS) promote the protection of primary and secondary saccharidic alcohols through a dehydration mechanism and in the absence of any strong protic or Lewis acid.

p-Methoxybenzyl trityl ether (p-MBTE): A new and improved tritylating reagent

p-Methoxybenzyl trityl ether (p-MBTE), synthesized for the first time from trityl chloride and p-methoxybenzyl alcohol, is utilized as a tritylating agent for a variety of alcohols, under neutral conditions, in 10-30 min. and excellent yields.

DIFFERENT REACTIVITIES OF ACETYLATED exo- AND endo-CYANOETHYLIDENE DERIVATIVES IN GLYCOSYLATION REACTIONS

The condensation of acetylated 1-(endo-cyano)ethylidene derivatives having the D-gluco, D-xylo, and D-galacto configurations (2-6) with a primary (8) and a secondary (9) trityl derivative was more rapid than for the corrensponding exo-isomers.This difference in reactivity is explained on the basis of differences in conformation.