114861-16-4

Basic information

• Product Name: Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• Synonyms: Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS NO: 114861-16-4
• Molecular Weight: 560.664
• Mol File: 114861-16-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester(114861-16-4)
• EPA Substance Registry System: Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester(114861-16-4)

Safety Data

• Hazardous Substances Data: 114861-16-4(Hazardous Substances Data)

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 114861-14-2 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose 
• 87-72-9 D-Xylose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 532-20-7 D-xylofuranose 

Downstream Products

• 216976-72-6 Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-71-5 Benzoic acid (3R,4R,5S)-4-azido-2-methoxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-62-4 3-azido-5-O-(4-phenylbenzyl)-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 216976-57-7 3-azido-3-deoxy-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 58699-62-0 3'-Azido-3'-deoxyadenosine 
• 23345-80-4 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 2504-55-4 3'-amino-3'-deoxyadenosine 
• 216976-56-6 ((3aR,5S,6R,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane 

Relevant articles and documents

Computer Modelling and Synthesis of Deoxy and Monohydroxy Analogues of a Ribitylaminouracil Bacterial Metabolite that Potently Activates Human T Cells

5-(2-Oxopropylideneamino)-6-d-ribitylaminouracil (5-OP-RU) is a natural product formed during bacterial synthesis of vitamin B2. It potently activates mucosal associated invariant T (MAIT) cells and has immunomodulatory, inflammatory, and anticancer properties. This highly polar and unstable compound forms a remarkably stable Schiff base with a lysine residue in major histocompatibility complex class I–related protein (MR1) expressed in antigen-presenting cells. Inspired by the importance of the ribityl moiety of 5-OP-RU for binding to both MR1 and the T cell receptor (TCR) on MAIT cells, each OH was removed in silico. DFT calculations and MD simulations revealed a very stable hydrogen bond between the C3′?OH and uracil N1H, which profoundly restricts flexibility and positioning of each ribityl-OH, potentially impacting their interactions with MR1 and TCR. By using deoxygenation strategies and kinetically controlled imine formation, four monodeoxyribityl and four monohydroxyalkyl analogues of 5-OP-RU were synthesised as new tools for probing T cell activation mechanisms.

Glycosamino acids: New building blocks for combinatorial synthesis

In order to produce inexpensive, chemically diverse carbohydrate building blocks more amenable for use in combinatorial organic synthesis, amine and carboxylic acid functional groups were incorporated into several monosaccharides. A series of 12 new glycosamino acids was prepared from commercially available starting materials. Conventional peptide synthesis solution coupling techniques were used to ligate glycosamino acids, producing oligomeric 'glycotides'. Finally, a library of glycotides was produced by coupling of a glycosamino acid mixture to a rigid template.