154172-46-0

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 1242653-93-5 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl acetate 
• 160701-85-9 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-β-D-glucopyranose 
• 154127-55-6 2,3,4,6-tetra-O-benzyl-β-1-C-(2-thiazolyl)-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 154127-57-8 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole 
• 154127-56-7 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-(2-thiazolyl)-α-D-glucopyranose 

Downstream Products

• 113019-43-5 2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose 

Relevant academic research and scientific papers

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.

Multigram scale synthesis of formyl tetra-O-benzyl-β-D-C-glucopyranoside using benzothiazole as a formyl group equivalent

The addition of 2-lithiobenzothiazole to D-gluconolactone followed by deoxygenation of the resulting ketose affords a mixture of benzothiazolyl α- and β-D-glucopyranoside; treatment of this mixture with sodium methoxide gives the β-anomer from which the title aldehyde is obtained in a pure form by transformation of the benzothiazole ring into the formyl group.

Selectivity in the SmI2-induced deoxygenation of thiazolylketoses for formyl C-glycoside synthesis and revised structure of C-ribofuranosides

Deoxygenation of thiazolylketose acetates using SmI2-(CH2OH)2 or TMSOTf-Et3SiH affords thiazolyl C-glycosides with opposite α/β ratios. Examination of the thiazolyl α- and β-C-ribofuranoside pair by NOE experime

Thiazole-based synthesis of formyl C-glycosides

A method for the installation of the formyl group at the anomeric position of pyranoses and furanoses starting from the corresponding lactones has been developed. The strategy involves the addition of 2-lithiothiazole to the sugar lactone, followed by the silane reduction of the acetylated resultant ketol and the unmasking of the formyl group from the thiazole ring. All steps have been studied in some details to improve chemical efficiency and stereochemical control. Hence, reversed α:β ratios of ketols were found in kinetic and thermodynamic mixtures, the former being consistent with a steric effect control of the substituents and the latter by the electronic effect of the ring oxygen. Seven sugar aldehydes with different D-pyranosidic (2,3,4,6-tetra-O-benzyl-gluco, -galacto, and -manno, 2-azido-3,4,6-tri-O-benzyl-2-deoxy-galacto) and D-furanosidic moieties (5-O-benzyl-2,3-isopropylidene-ribo; 2,3,5-tri-O-benzyl-ribo; 2,3:5,6-di-O-isopropylidene-manno) were prepared in 52-65% isolated overall yield from the corresponding lactone.

Thiazole-based synthesis of C-glycosyl aldehydes

The formylation at the anomeric carbon of the model sugars 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3:5,6-di-O-isopropylidene-D-mannofuranose is carried out by addition of 2-lithiothiazole to the corresponding lactones followed by reductive dehydroxyl