114219-26-0

Basic information

• Product Name: methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside
• Synonyms: methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside
• CAS NO: 114219-26-0
• Molecular Weight: 618.748
• Mol File: 114219-26-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside(114219-26-0)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside(114219-26-0)

Safety Data

• Hazardous Substances Data: 114219-26-0(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 126360-05-2 methyl 6-deoxy-6-(methylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 126360-06-3 methyl 6-deoxy-6-(ethylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 72471-11-5 methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 1555636-12-8 C₄₉H₅₉N₃O₇ 
• 1449009-45-3 ((2S,3R,4R,5S,6R)-1-benzyl-3,4,5-tris(benzyloxy)-6-vinylpiperidin-2-yl)methanol 
• 1449009-43-1 ((2S,3R,4R,5S,6R)-1-benzyl-3,4,5-tris(benzyloxy)-6-ethylpiperidin-2-yl)methanol 
• 1449009-42-0 ((2S,3R,4R,5S,6S)-6-allyl-1-benzyl-3,4,5-tris(benzyloxy)piperidin-2-yl)methanol 
• 1449009-33-9 (3R,4R,5R,6S,7S)-1-benzyl-4,5,6-tris(benzyloxy)-7-vinylazepan-3-ol 
• 1449009-32-8 (3R,4R,5R,6S,7R)-1-benzyl-4,5,6-tris(benzyloxy)-7-vinylazepan-3-ol 
• 1354826-67-7 (2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate 
• 1354826-69-9 (3R,4R,5R,6S,7S)-7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-yl 4-nitrobenzoate 
• 1449009-31-7 (3R,4R,5R,6S,7R)-1-benzyl-4,5,6-tris(benzyloxy)-7-ethylazepan-3-ol 

Relevant articles and documents

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Skeletal rearrangement of seven-membered iminosugars: Synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors

The mirror image of natural product (+)-adenophorine along with its 1-epi-, 1-homo-analogs and other derivatives have been synthesized and evaluated as glycosidase inhibitors. The synthetic strategy is based on the skeletal rearrangement of tetrahydroxylated C-alkyl azepanes obtained via a Staudinger/azaWittig/alkylation sequence starting from a sugar-derived azidolactol. Several organometallic species have been investigated for the alkylation step including organomagnesium, organolithium, organozinc, organoaluminum and organocerium reagents. While diallylzinc proved to be the most efficient to introduce an allyl substituent, disappointing results were obtained with the other organometallic species leading either to lower yields or no reaction. Enzymatic assays indicate that (-)-adenophorine is a moderate α-l-fucosidase inhibitor.

Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases

Disaccharides of 1-thioglycosides, an important class of glycomimics, can be synthesized by direct S-alkylation in exceptionally high yields when iminophosphorane bases are employed. The reaction conditions employed appear to be general and stereospecific