112219-66-6

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 1826-67-1 vinyl magnesium bromide 
• 168253-07-4 (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran 
• 166828-15-5 4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-1-eno-3-ulopyranose 
• 1193390-93-0 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(1-(phenylsulfonyl)vinyl)tetrahydro-2H-pyran 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 676241-01-3 Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester 
• 343315-86-6 Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester 
• 343315-92-4 ((1R,2S,3R,4R,5S)-2,3,4-Tris-benzyloxy-5-methoxy-cyclooctyl)-methanol 
• 343315-91-3 ((1S,2S,3R,4R,5S)-2,3,4-Tris-benzyloxy-5-methoxy-cyclooctyl)-methanol 
• 343315-90-2 (1S,2R,3R,4R)-2,3,4-tribenzyloxy-1-methoxy-5-methylenecyclooctane 
• 343315-88-8 (1R,2S,3R,4R,5S)-2,3,4-tribenzyloxy-5-methoxycycloocta-1-ol 
• 343315-89-9 (2R,3S,4S,5S)-2,3,4-tribenzyloxy-5-methoxycyclooctan-1-one 
• 261956-04-1 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol 
• 676241-18-2 (2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester 
• 676241-08-0 (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester 
• 676241-20-6 (2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester 
• 676241-09-1 (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester 
• 676241-19-3 (2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid 
• 676241-10-4 (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid 

Relevant academic research and scientific papers

Practical Gram-Scale Synthesis of Either α- Or β-Anomer of C -Vinyl Glycosides

The synthesis C -vinyl glycosides, useful intermediates for the synthesis of C -glycoconjugates, was carried out on gram-scale by controlled reduction of the corresponding ethynyl derivatives in good to excellent yields in different carbohydrate series.

Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors

With anticipation of the improvement in biological aspects in our SGLT2 program, novel pyridazinyl and thiazolyl analogs were designed and efficiently synthesized. The installation of the pyridazine ring at the anomeric carbon of d-glucopyranose was carried out in a stereoselective fashion. On the other hand, a series of thiazolyl analogs was also synthesized through a coupling reaction between perbenzyl gluconolactone 9 and 2-lithiothiazole. Biological activities of the compounds thus prepared were evaluated by the in vitro SGLT2 inhibition assay. Considering assay results, the novel benzylpyridazinyl and benzylthiazolyl analogs, disclosed in this article, could be a quick reference to prospective SGLT2 inhibitors useful for pharmacotherapy.

A Mitsunobu route to C-glycosides

C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach

PHENYLAZETIDINONE DERIVATIVES

Various azetidinone derivatives are described, as are pharmaceutical compositions containing these compounds and methods of treatment of diseases using these compounds. Other embodiments are also described.

Reinvestigation of the synthesis of per-benzylated glycosylethenes: A new result

Addition of vinylmagnesium bromide on the perbenzylated glucono-1, 5-lactone gave, after reduction with Et3SiH/BF3· Et2O, a mixture of the desired β-C-vinyl glucoside 1 and the unexpected β-C-but-3-enyl glucoside 3 resulting from double addition of vinylmagnesium bromide on the lactone. Similar results have been obtained with the perbenzylated galactono-1,5-lactone. This side reaction was then been explored to prepare β-C-but-3-enyl glycosides and other β-C-glycosyl derivatives by employing different Grignard reagents. An alternative approach to the per-benzylated glycosylethenes has been studied and compared.

A concise C-glycosyl amino acid synthesis by alkenyl C-glycoside-vinyloxazolidine cross-metathesis. Synthesis of glycosyl serine, asparagine and hydroxynorvaline isosteres

A convergent synthesis has been developed to afford C-linked glycosyl amino acids by cross-metathesis of vinyl, allyl, and butenyl C-glycosides with N-Boc-vinyloxazolidine using the Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylideneruthenium carbene. The method has been employed to introduce through an α-linkage, an α-aminopentanoic acid chain at the anomeric carbon of β-D-C-gentiobiose to give a totally artificial glycosyl α-amino acid of a disaccharide. This compound represents the isostere of the α-linked glycosylasparagine moiety of the natural glycopeptide nephritogenoside.